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【结 构 式】

【分子编号】10272

【品名】[[Amino(imino)methyl]sulfanyl]methane

【CA登记号】2986-19-8

【 分 子 式 】C2H6N2S

【 分 子 量 】90.14912

【元素组成】C 26.65% H 6.71% N 31.07% S 35.57%
与该中间体有关的原料药合成路线共 20 条
合成路线1合成路线2合成路线3合成路线4合成路线5合成路线6合成路线7合成路线8合成路线9合成路线10合成路线11合成路线12合成路线13合成路线14合成路线15合成路线16合成路线17合成路线18合成路线19合成路线20

合成路线1

该中间体在本合成路线中的序号：(I)

The synthesis of [14C]-labeled 15-deoxyspergualin trihydrochloride has been reported: The condensation of [14C]-labeled S-methylisothiourea (I) with 7-aminoheptanoic acid (II) by means of NaOH in water gives 7-guanidinoheptanoic acid (III), which is treated with Dowex 50W resin (H+ form) in refluxing methanol yielding the corresponding methyl ester (IV). The reaction of (IV) with concentrated NH4OH affords the amide (V), which is finally condensed with glyoxyloxyspermidine (VI) by means of glutaric acid in hot water (60 C), and purified by chromatography over Sephadex CM-25 (Na+ form).

参考文献 中间体
合成目标
【1】 Dischino, D.D.; Synthesis of carbon-14 labeled (±) 15-deoxyspergualin trihydrochloride. J Label Compd Radiopharm 1995, 36, 11, 1097.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(I) 44636 [[amino(imino)methyl]sulfanyl]methane C2H6N2S 详情 详情
(II) 10273 7-Aminoheptanoic acid 929-17-9 C7H15NO2 详情 详情
(III) 10274 7-[[Amino(imino)methyl]amino]heptanoic acid C8H17N3O2 详情 详情
(III) 44637 7-[[amino(imino)methyl]amino]heptanoic acid C8H17N3O2 详情 详情
(IV) 10275 methyl 7-[[amino(imino)methyl]amino]heptanoate C9H19N3O2 详情 详情
(IV) 44638 methyl 7-[[amino(imino)methyl]amino]heptanoate C9H19N3O2 详情 详情
(V) 10270 7-[[Amino(imino)methyl]amino]heptanamide C8H18N4O 详情 详情
(V) 44639 7-[[amino(imino)methyl]amino]heptanamide C8H18N4O 详情 详情
(VI) 10271 N-[4-[(3-Aminopropyl)amino]butyl]-2,2-dihydroxyacetamide C9H21N3O3 详情 详情

合成路线2

该中间体在本合成路线中的序号：(I)

The condensation of S-methylisothiourea (I) with trans-4-(aminomethyl)cyclohexanecarboxylic acid (II) by means of NaOH in water gives trans-4-(guanidinomethyl)cyclohexanecarboxylic acid (III) (I), which is esterified with benzyl salicylate (IV) by means of dicyclohexylcarbodiimide (DCC) or SOCl2 yielding 2-benzyloxycarbonylphenyl trans-4-(guanidinomethyl)cyclohexanecarboxylate (V). Finally, this compound is treated with cyclodextrin in aqueous solution to afford the corresponding complex.

参考文献 中间体
合成目标
【1】 Umeyama, M.; Ooi, Y.; Muramutu, M.; Miyataka, H.; Nakajima, T.; Satoh, T.; Medicinal chemical studies on synthetic protease i. Chem Pharm Bull 1985, 33, 2, 647.
【2】 Villani, F.J. (Schering Corp.); Antihistaminic 11-(4-piperidylidene)-5H-benzo-[5,6. US 4282233 .
【3】 Prous, J.; Castaner, J.; TA-903. Drugs Fut 1987, 12, 5, 451.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(II) 23058 4-(aminomethyl)cyclohexanecarboxylic acid 1197-18-8 C8H15NO2 详情 详情
(III) 23059 4-([[amino(imino)methyl]amino]methyl)cyclohexanecarboxylic acid C9H17N3O2 详情 详情
(IV) 23060 benzyl salicylate 118-58-1 C14H12O3 详情 详情
(V) 23061 benzyl 2-([[4-([[amino(imino)methyl]amino]methyl)cyclohexyl]carbonyl]oxy)benzoate C23H27N3O4 详情 详情

合成路线3

该中间体在本合成路线中的序号：(V)

1) By methanolysis of 2,6-dichlorophenylacetonitrile (I) by means of H2SO4 to methyl 2,6-dichlorophenylacetate (II), which is then condensed with guanidine (A) in isopropanol. 2) By condensation of S-methylisothiourea (V) with 2,6-dichlorophenylacetyl chloride (VI) in acetone to afford S-methyl-N-(2,6-dichlorophenylacetyl)isothiourea (VII); this product is then treated with ammonia in isopropanol. 3) By condensation of 2,6-dichlorophenylacetic acid (VIII) with guanidine (A) in toluene.

参考文献 中间体
合成目标
【1】 Arrigoni-Martelli, E.; Castaner, J.; BS 100-141. Drugs Fut 1976, 1, 4, 167.
【2】 Bream, J.B.; et al.; Substituted phenylacetylguanidines: A new class of antihypertensive agents. Arzneim-Forsch Drug Res 1975, 25, 10, 1477.
【3】 Bream, J.B.; et al. (Novartis AG); Substituted phenylacethyl derivatives of guanidine, O-alkylisoureas, S-alkylisothioureas and p-benzylalkylisothioureas. DE 179348; FR 1584670; GB 1235723; US 3632645 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 14790 Guanidine 113-00-8 CH5N3 详情 详情
(I) 18202 2-(2,6-dichlorophenyl)acetonitrile; 2,6-Dichlorophenylacetonitrile 3215-64-3 C8H5Cl2N 详情 详情
(II) 40327 methyl 2-(2,6-dichlorophenyl)acetate 54551-83-6 C9H8Cl2O2 详情 详情
(V) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(VI) 40329 2-(2,6-dichlorophenyl)acetyl chloride C8H5Cl3O 详情 详情
(VII) 40330 1,3-dichloro-2-(2-[[imino(methylsulfanyl)methyl]amino]-2-oxoethyl)benzene C10H10Cl2N2OS 详情 详情
(VIII) 40328 2-(2,6-dichlorophenyl)acetic acid 6575-24-2 C8H6Cl2O2 详情 详情

合成路线4

该中间体在本合成路线中的序号：(IV)

The reaction of 5-isoquinolinesulfonyl chloride (I) with ethyldiamine (II) in methylene chloride gives N-(2-aminoethyl)isoquinoline-5-sulfonamide (III), which is then condensed with S-methylisothiourea sulfate (IV) by means of NaOH at 80 C.

参考文献 中间体
合成目标
【1】 Asano, T.; Hidaka, H.; Vasodilatory action of HA-1004 [N-(2-guanidinoethyl)-5-isoquinolinesulfonamide], a novel calcium antagonist with no efect on cardiac function. J Pharmacol Exp Ther 1984, 231, 1, 141.
【2】 Koch, H.; Castaner, J.; HA-1004. Drugs Fut 1985, 10, 10, 815.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 27362 5-isoquinolinesulfonyl chloride 84468-15-5 C9H6ClNO2S 详情 详情
(II) 14754 ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine 107-15-3 C2H8N2 详情 详情
(III) 27363 N-(2-aminoethyl)-5-isoquinolinesulfonamide C11H13N3O2S 详情 详情
(IV) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情

合成路线5

该中间体在本合成路线中的序号：(IX)

The reaction of 2,3-dichlorobenzoic acid (I) with oxalyl chloride in dichloromethane gives the acyl chloride (II), which is condensed with labeled copper cyanide (III) by means of KI in refluxing xylene to yield the 2,3-dichlorobenzoyl cyanide (IV). The condensation of (IV) with labeled aminoguanidine (V) by means of sulfuric acid in acetonitrile/water affords adduct (VI), which is finally cyclized by refluxing under the conditions of the preceding reaction to provide the target labeled diaminotriazine. The intermediate labeled copper cyanide (III) has been obtained by reaction of CuSO4 with labeled potassium cyanide (VII) and Na2S2O5 in hot water. The intermediate labeled aminoguanidine (V) has been obtained by methylation of thiourea (VIII) with dimethyl sulfate in boiling water to give S-methylisothiourea (IX), which is finally treated with hydrazine (X) and NaOH in water.

参考文献 中间体
合成目标
【1】 Manning, C.O.; et al.; Synthesis of stable isotopically labelled versions of lamotrigine and its methylated metabolite. J Label Compd Radiopharm 2002, 45, 7, 611.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 24007 2,3-dichlorobenzoic acid 50-45-3 C7H4Cl2O2 详情 详情
(II) 24008 2,3-dichlorobenzoyl chloride 2905-60-4 C7H3Cl3O 详情 详情
(III) 56856 Copper (I) cyanide; Cuprous cyanide 544-92-3 CCuN 详情 详情
(III) 56861 cyanocopper CCuN 详情 详情
(IV) 24009 2-(2,3-dichlorophenyl)-2-oxoacetonitrile; 2,3-Dichlorobenzoylcyanide 77668-42-9 C8H3Cl2NO 详情 详情
(IV) 56862 2-(2,3-dichlorophenyl)-2-oxoacetonitrile C8H3Cl2NO 详情 详情
(V) 56857 　 CH6N4 详情 详情
(V) 56866 　 CH6N4 详情 详情
(VI) 56858 1,2-dichloro-3-{cyano[(Z)-2-(diaminomethylene)hydrazono]methyl}benzene C9H7Cl2N5 详情 详情
(VI) 56867 1,2-dichloro-3-{cyano[(Z)-2-(diaminomethylene)hydrazono]methyl}benzene C9H7Cl2N5 详情 详情
(VII) 56859 Potassium cyanide 151-50-8 CKN 详情 详情
(VII) 56860 cyanopotassium CKN 详情 详情
(VIII) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(VIII) 56863 thiourea CH4N2S 详情 详情
(IX) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(IX) 56864 {[amino(imino)methyl]sulfanyl}methane C2H6N2S 详情 详情
(X) 27344 hydrazine 302-01-2 H4N2 详情 详情
(X) 56865 hydrazine H4N2 详情 详情

合成路线6

该中间体在本合成路线中的序号：

This compound can be prepared by two related ways: 1) The diazotation of L-serine methyl ester (I) with NaNO2 - HCl gives methyl (S)-glycerate (II), which by reaction with 2,2-dimethoxypropane and p-toluenesulfonic acid (or acetone and ZnCl2) is converted to methyl (S)-O-isopropylideneglycerate (III). The reduction of (III) with LiAlH4 in refluxing ether affords (S)-2,3-O-isopropylideneglycerol (IV), which by reaction with tosyl chloride in pyridine is converted to the corresponding tosylate (V). The partial hydrolysis of (V) with HCl in acetone affords (S)-glycerol-1-tosylate (VI), which is finally condensed with 1-phenylpiperazine (VII) in refluxing benzene. 2) The partial hydrolysis of (S)-2,3-epoxypropyl tosylate (VIII) with HCl as before gives the glycerol tosylate (VI), already obtained.

参考文献 中间体
合成目标
【1】 Borsa, M.; Tonon, G.; Malandrino, S. (Dompé Farm. SpA); Optically active compounds with antitussive and central sedative activity, a process for the preparation thereof and compositions containing the same. EP 0147847; US 4699911; US 4764515 .
【2】 Giani, R.; Marione, E.; Melillo, G.; Borsa, M.; Tonon, G.C.; Synthesis and pharmacological screening of new phenylpiperazinepropane derivatives and their enantiomers. Arzneim-Forsch Drug Res 1988, 38, 8, 1139-41.
【3】 Prous, J.; Castaner, J.; LEVDROPROPIZINE < Rec INN >. Drugs Fut 1989, 14, 6, 522.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(I) 20915 methyl (2S)-2-amino-3-hydroxypropanoate 5680-80-8 C4H9NO3 详情 详情
(II) 20916 methyl (2R)-2,3-dihydroxypropanoate C4H8O4 详情 详情
(III) 20917 methyl (4R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 52373-72-5 C7H12O4 详情 详情
(IV) 12709 [(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methanol 22323-82-6 C6H12O3 详情 详情
(V) 20919 [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate 23788-74-1 C13H18O5S 详情 详情
(VI) 20920 (2R)-2,3-dihydroxypropyl 4-methylbenzenesulfonate C10H14O5S 详情 详情
(VII) 10756 N-Phenylpiperazine; 1-Phenylpiperazine; Phenyl piperazine 92-54-6 C10H14N2 详情 详情
(VIII) 16242 (2R)oxiranylmethyl 4-methylbenzenesulfonate; (2R)-(-)-Glycidyl tosylate 113826-06-5 C10H12O4S 详情 详情

合成路线7

该中间体在本合成路线中的序号：(VII)

Nitroacetaldehyde oxime (I) is formed from nitromethane in the presence of NaOH and is converted in acidic media with 2-aminobenzoic acid (II) to 2-(2-nitroethylideneamino)benzoic acid (III). Cyclization of (III) in acetic anhydride by means of potassium acetate yields 4-hydroxy-3-nitroquinoline (IV), which is converted to 4-chloro-3-nitroquinoline (V) in boiling POCl3. Reaction of (V) with morpholinecarboximidamide (VIII) (formed from morpholine (VI) and S-methylisothiourea hemisulfate (VII) in ethanol) affords troquidazole.

参考文献 中间体
合成目标
【1】 Berényi, E.; Varga, L.; Pallos, L.; Petöcz, L.; Ladányi, L.; Tömpe, P.; Hartai, E.; Kovács, A. (Egis Pharmaceuticals Ltd.); N-(3-Nitroquinolin-4-yl)guanidine derivatives as radiosensitizers. (EGIS Pharm., Ltd.). BE 0904864; CH 668069; ES 8707231; GB 2176185; JP 1987048668; US 4652562 .
【2】 Nógrádi, M.; Berényi, E.; Blaskó, G.; Troquidazole. Drugs Fut 1992, 17, 5, 384.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11660 2-Nitroacetaldehyde oximesodium salt C2H3N2NaO3 详情 详情
(II) 11661 2-Aminobenzoic acid;Anthranilic acid; o-Aminobenzoic acid 118-92-3 C7H7NO2 详情 详情
(III) 11662 2-[[(E)-2-Nitroethylidene]amino]benzoic acid C9H8N2O4 详情 详情
(IV) 11663 3-Nitro-4-quinolinol; 3-Nitro-quinolin-4-ol C9H6N2O3 详情 详情
(V) 11664 4-Chloro-3-nitroquinoline C9H5ClN2O2 详情 详情
(VI) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(VII) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(VIII) 11667 4-Morpholinecarboximidamide C5H11N3O 详情 详情

合成路线8

该中间体在本合成路线中的序号：(I)

The reaction of S-methylisothiourea (I) with Boc2O by means of NaHCO3 gives the N-Boc protected isothiourea (II), which is condensed with 1,4-butanediamine (III) in hot THF to yield the guanidine derivative (IV). The acylation of the amino group of (IV) with 3,4-dimethoxycinnamoyl chloride (V) with THF/DMF affords the corresponding amide (VI), which is deprotected with TFA to provide N-(4-guanidinobutyl)-3,4-dimethoxycinnamamide (VII). Finally, the guanidino group of (VII) is alkylated with 3-methyl-2-butenyl bromide (VIII) catalyzed by DMAP in THF to provide the target, caracasanamide.

参考文献 中间体
合成目标
【1】 Delle Monache, G.; Delle Monache, F.; Botta, B.; Bonnevaux Castillo, S.; Espinal, R.; De Luca, C.; Carmignani, M. (Consiglio Nazionale delle Ricerche); Guanidine derivs. having hypotensive activity, compsn. containing them, and process for obtaining them. EP 0330629; JP 1990003661; US 5059624 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(II) 22345 tert-butyl (E)-[(tert-butoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate C12H22N2O4S 详情 详情
(III) 42070 1,4-butanediamine; 4-aminobutylamine 110-60-1 C4H12N2 详情 详情
(IV) 53109 tert-butyl (Z)-[(4-aminobutyl)amino][(tert-butoxycarbonyl)amino]methylidenecarbamate n/a C15H30N4O4 详情 详情
(V) 33601 (E)-3-(3,4-dimethoxyphenyl)-2-propenoyl chloride C11H11ClO3 详情 详情
(VI) 53110 tert-butyl (Z)-[(tert-butoxycarbonyl)amino][(4-{[(E)-3-(3,4-dimethoxyphenyl)-2-propenoyl]amino}butyl)amino]methylidenecarbamate n/a C26H40N4O7 详情 详情
(VII) 53111 (E)-N-(4-{[amino(imino)methyl]amino}butyl)-3-(3,4-dimethoxyphenyl)-2-propenamide n/a C16H24N4O3 详情 详情
(VIII) 12989 4-Bromo-2-methyl-2-butene; 1-Bromo-3-methyl-2-butene 870-63-3 C5H9Br 详情 详情

合成路线9

该中间体在本合成路线中的序号：

The synthesis of MD-39-AM (V) was carried out as follows: From 2-chloronicotinic acid (as its acyl chloride) (I) and thiourea in triethylamine (1:1:2), compound (II) was obtained. However, in order to avoid the substitution of 2-Cl by sulfur, 2-methylisothiourea was used. By boiling a solution of (II) in dimethylformamide (DMF) for 15 min, (III) (87%) was obtained. Reaction of (III) with phosphorous oxychloride gave 4-chloro-2-(methylthio)pyrido[2,3-d]pyrimidine (IV) (90%). By reacting (IV) with aniline in ethanol, MD-39-AM was obtained.

参考文献 中间体
合成目标
【1】 Martinez-Merino, V.; Ochoa, M.C.; Fernandez, F.J.; Artigas, P.; Monge, A.; Bellver, C.; Sanmartin, C.; Fernandez-Alvarez, E.; 2-Arylamino-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidines: Synthesis and diuretic activity. Eur J Med Chem 1989, 24, 209.
【2】 Martinez-Merino, V.; Monge, A.; Sanmartin, C.; MD-39-AM. Drugs Fut 1992, 17, 2, 107.
【3】 Ochoa, M.C.; Fernández, F.J.; Sanmartín, C.; Monge, A.; Martínez-Merino, V.; Bellver, C.; Artigas, P.; Diuretic and hypotensive activities of 4-anilino derivatives of 2-methylthiopyrido[2,3-d]pyrimidines. Arzneim-Forsch Drug Res 1990, 40, 11, 1230-3.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(I) 15224 2-chloronicotinoyl chloride 49609-84-9 C6H3Cl2NO 详情 详情
(II) 15225 2-chloro-3-([[imino(methylsulfanyl)methyl]amino]carbonyl)pyridine C8H8ClN3OS 详情 详情
(III) 15226 2-(methylsulfanyl)pyrido[2,3-d]pyrimidin-4-ol C8H7N3OS 详情 详情
(IV) 15227 4-chloropyrido[2,3-d]pyrimidin-2-yl methyl sulfide; 4-chloro-2-(methylsulfanyl)pyrido[2,3-d]pyrimidine C8H6ClN3S 详情 详情

合成路线10

该中间体在本合成路线中的序号：(XV)

4) The selective deacetylation of 4-O,5-N,7-O,8-O,9-O-pentaacetyl-2,3-didehydro-2-deoxyneuraminic acid (XI) with boron trifluoride ethearate in benzene/methanol gives the 4-deacetyl derivative (XII), which is treated with trifluoromethanesulfonic anhydride in dichloromethane and with sodium azide in DMF to obtain the 4-azido-4-deoxy derivative (XIII). The reduction of (XIII) with H2S in pyridine affords the corresponding 4-amino derivative (XIV), which is finally condensed with S-methylisothiourea in water and saponified through Dowex 50W x 8 in aqueous NH4OH.

参考文献 中间体
合成目标
【1】 Von Itzstein, L.M.; Wu, W.-Y.; Phan, T.; Danylec, B.; Derivs. and analogues of 2-deoxy-2,3-didehydro-N-acetyl neuraminic acid and their use as antiviral agents. EP 0786458; WO 9116320 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 15985 methyl (2R,3S,4S)-3-(acetamido)-4-(acetoxy)-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate C20H27NO12 详情 详情
(XII) 15986 methyl (2R,3R,4S)-3-(acetamido)-4-hydroxy-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate C18H25NO11 详情 详情
(XIII) 15979 methyl (2R,3R,4S)-3-(acetamido)-4-azido-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate C18H24N4O10 详情 详情
(XIV) 15988 methyl (2R,3R,4S)-3-(acetamido)-4-amino-2-[(1S,2R)-1,2,3-tris(acetoxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate C18H26N2O10 详情 详情
(XV) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情

合成路线11

该中间体在本合成路线中的序号：(I)

An improved synthesis of [14C]-peldesine has been reported: The reaction of S-methyl-[14C]-isothiourea (I) with methyl chloroformate (II) by means of tetrabutylammonium bromide in dichloromethane gives N,N'-bis(methoxycarbonyl)-S-methyl-[14C]-isothiourea (III). This compound is condensed with 3-amino-4-(3-pyridylmethyl)-1H-pyrrole-2-carboxylic acid methyl ester (IV) by means of acetic acid in methanol yielding the labeled guanidine (V). The cyclization of (V) by means of sodium methoxide in methanol affords the carbamate precursor (VI), which is finally deprotected with NaOH in hot water.

参考文献 中间体
合成目标
【1】 Elliott, A.J.; Kwong, C.D.; Montgomery, J.A.; An improved synthesis of 9-(3-pyridylmethyl)-[2-14C]-9-deazaguanine. J Label Compd Radiopharm 1998, 41, 10, 879.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(I) 44636 [[amino(imino)methyl]sulfanyl]methane C2H6N2S 详情 详情
(II) 16993 methyl chlorocarbonate;Carbonochloridic acid methyl ester；[(chlorocarbonyl)oxy]methane；methyl chloroformate 79-22-1 C2H3ClO2 详情 详情
(III) 28696 methyl (Z)-[(methoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate C6H10N2O4S 详情 详情
(III) 45292 methyl (Z)-[(methoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate C6H10N2O4S 详情 详情
(IV) 16030 methyl 3-amino-4-(3-pyridinylmethyl)-1H-pyrrole-2-carboxylate C12H13N3O2 详情 详情
(V) 28697 methyl 3-([bis[(methoxycarbonyl)amino]methylene]amino)-4-(3-pyridinylmethyl)-1H-pyrrole-2-carboxylate C17H19N5O6 详情 详情
(V) 45293 methyl 3-([bis[(methoxycarbonyl)amino]methylene]amino)-4-(3-pyridinylmethyl)-1H-pyrrole-2-carboxylate C17H19N5O6 详情 详情
(VI) 28698 methyl 4-oxo-7-(3-pyridinylmethyl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-ylcarbamate C14H13N5O3 详情 详情
(VI) 45294 methyl 4-oxo-7-(3-pyridinylmethyl)-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-ylcarbamate C14H13N5O3 详情 详情

合成路线12

该中间体在本合成路线中的序号：

The reaction of 4-chlorobenzoylhydrazide (I) with S-methyl isothiourea sulfate in aqueous NaOH gave guanidine (II) which, on heating at 220 C, was converted into aminotriazole (III). Subsequent condensation with methyl isothiocyanate in DMF gave thiocarbonyl triazole (IV). Finally, cyclization with diethoxymethyl acetate at 90 C provided the target triazolotriazine.

参考文献 中间体
合成目标
【1】 Akahoshi, F.; et al.; Synthesis and pharmacological activity of triazolo[1,5-a]triazine derivatives inhibiting eosinophilia. J Med Chem 1998, 41, 16, 2985-2993.
【2】 Naito, Y.; et al.; Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia. J Med Chem 1996, 39, 15, 3019-3029.
【3】 Akahoshi, F.; Okada, T.; Takeda, S.; Naito, Y.; Fukaya, C.; Kuwahara, S.; Kajii, M.; Nishimura, H.; Sugiura, M. (Welfide Corporation); Triazole derivs. and pharmaceutical use thereof. EP 0710654; JP 1995082270; JP 1995097321; JP 1995101942; US 5750545; WO 9503286 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(I) 18216 4-chlorobenzohydrazide; p-chloro-benzoylhydrazine 536-40-3 C7H7ClN2O 详情 详情
(II) 18217 2-(4-chlorobenzoyl)-1-hydrazinecarboximidamide C8H9ClN4O 详情 详情
(III) 18218 5-(4-chlorophenyl)-1H-1,2,4-triazol-3-ylamine; 5-(4-chlorophenyl)-1H-1,2,4-triazol-3-amine C8H7ClN4 详情 详情
(IV) 18219 5-amino-3-(4-chlorophenyl)-N-methyl-1H-1,2,4-triazole-1-carbothioamide C10H10ClN5S 详情 详情
(V) 17661 Diethoxymethyl acetate 14036-06-7 C7H14O4 详情 详情

合成路线13

该中间体在本合成路线中的序号：(IV)

The condensation of 4-fluorobenzaldehyde (I) with 4-methyl-3-oxopentanoic acid ethyl ester (II) by means of piperidine/AcOH in refluxing benzene gives the corresponding benzylidene derivative (III), which is cyclized with S-methylisothiourea (IV) and oxidized with DDQ, affording the pyrimidine derivative (V). The oxidation of (V) with m-chloroperbenzoic acid (m-CPBA) gives the expected methanesulfonyl derivative (VI), which is treated first with methylamine and then with methanesulfonyl chloride to provide the N-methylmethanesulfonamide (VII). The reduction of the ester group of (VII) with DIBAL in toluene, followed by selective oxidation of the resulting alcohol with TPAP, affords the aldehyde (VIII), which is submitted to a Wittig condensation with the phosphorane (IX) in acetonitrile to give the protected heptenoate (X). The deprotection of (X) with FH and the controlled reduction of the resulting keto alcohol with Et2BOMe and NaBH4 affords the chiral dihydroxyheptenoate (XI), which is hydrolyzed with NaOH in ethanol, yielding the corresponding sodium salt (XII). Finally, this compound is treated with calcium chloride.

参考文献 中间体
合成目标
【1】 Watanabe, M.; et al.; Synthesis and biological activity of methanesulfonamide pyrimidine- and N-methanesulfonyl pyrrole-substituted 3,5-dihydroxy-6-heptenoates, a novel series of HMG-CoA reductase inhibitors. Bioorg Med Chem 1997, 5, 2, 437.
【2】 Castañer, J.; Graul, A.; ZD-4522. Drugs Fut 1999, 24, 5, 511.
【3】 Hirai, K.; Ishiba, T.; Koike, H.; Watanabe, M. (Shionogi & Co. Ltd.); Pyrimidine derivs. as HMG-CoA reductase inhibitors. EP 0521471; JP 1993178841; US 5260440 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 12337 4-fluorobenzaldehyde 459-57-4 C7H5FO 详情 详情
(II) 19408 ethyl 4-methyl-3-oxopentanoate 7152-15-0 C8H14O3 详情 详情
(III) 15877 ethyl (Z)-3-(4-fluorophenyl)-2-isobutyryl-2-propenoate C15H17FO3 详情 详情
(IV) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(V) 23879 ethyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfanyl)-5-pyrimidinecarboxylate C17H19FN2O2S 详情 详情
(VI) 23880 ethyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl)-5-pyrimidinecarboxylate C17H19FN2O4S 详情 详情
(VII) 23881 ethyl 4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-5-pyrimidinecarboxylate C18H22FN3O4S 详情 详情
(VIII) 23882 N-[4-(4-fluorophenyl)-5-formyl-6-isopropyl-2-pyrimidinyl]-N-methylmethanesulfonamide 147118-37-4 C16H18FN3O3S 详情 详情
(IX) 23884 methyl (3R)-3-[[tert-butyl(dimethyl)silyl]oxy]-5-oxo-6-(triphenylphosphoranylidene)hexanoate 147118-35-2 C31H39O4PSi 详情 详情
(X) 23883 methyl (3R,6E)-3-[[tert-butyl(dimethyl)silyl]oxy]-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-5-oxo-6-heptenoate 147118-38-5 C29H42FN3O6SSi 详情 详情
(XI) 23885 methyl (3R,5S,6E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoate 147118-40-9 C23H30FN3O6S 详情 详情
(XII) 23887 sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoate 147098-18-8 C22H27FN3NaO6S 详情 详情

合成路线14

该中间体在本合成路线中的序号：(II)

N-Boc-ethylenediamine (I) was treated with S-methylisothiourea (II) yielding guanidine (III). The Boc group of (III) was then cleaved by treatment with HCl.

参考文献 中间体
合成目标
【1】 Cozzi, P.; Beria, I.; Biasoli, G.; Caldarelli, M.; Capolongo, L.; Franzetti, C. (Pharmacia & Upjohn AB); Acryloyl substd. distamycin derivs., process for preparing them, and their use as antitumor and antiviral agents. WO 9804524 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 13241 N-Boc-ethylenediamine;tert-butyl (2-aminoethyl)carbamate；tert-butyl 2-aminoethylcarbamate; tert-Butyl n-(2-aminoethyl)carbamate 57260-73-8 C7H16N2O2 详情 详情
(II) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(III) 41436 tert-butyl 2-[[amino(imino)methyl]amino]ethylcarbamate C8H18N4O2 详情 详情
(IV) 41437 N-(2-aminoethyl)guanidine C3H10N4 详情 详情

合成路线15

该中间体在本合成路线中的序号：(XII)

Protection of 3-amino-5-methylphenol (I) with phthalic anhydride (II) provided the phthalimido derivative (III), which was alkylated with ethyl 4-bromobutyrate (IV) in the presence of K2CO3 to give the corresponding ether (V). Hydrazinolysis of the phthalimido group of (V) afforded the primary amine (VI), which was condensed with benzenesulfonyl chloride (VII), yielding sulfonamide (VIII). Saponification of the ethyl ester of (VIII) gave carboxylic acid (IX). After conversion to the mixed anhydride with isobutyl chloroformate and N-methylmorpholine, treatment with methanolic ammonia furnished amide (X). This was reduced to amine (XI) using LiAlH4 in THF. Finally, reaction of (XI) with S-methylisothiouronium sulfate (XII) in refluxing EtOH provided the target guanidine.

参考文献 中间体
合成目标
【1】 Weber, I.R.; Neidlein, R.; von der Saal, W.; Grams, F.; Leinert, H.; Strein, K.; Engh, R.A.; Kucznierz, R.; Diarylsulfonamides as selective, non-peptidic thrombin inhibitors. Bioorg Med Chem Lett 1998, 8, 13, 1613.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(II)) 11900 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride 85-44-9 C8H4O3 详情 详情
(I) 31435 3-amino-5-methylphenol C7H9NO 详情 详情
(III) 31436 2-(3-hydroxy-5-methylphenyl)-1H-isoindole-1,3(2H)-dione C15H11NO3 详情 详情
(IV) 11263 ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate 2969-81-5 C6H11BrO2 详情 详情
(V) 31437 ethyl 4-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-methylphenoxy]butanoate C21H21NO5 详情 详情
(VI) 31438 ethyl 4-(3-amino-5-methylphenoxy)butanoate C13H19NO3 详情 详情
(VII) 14713 benzenesulfonyl chloride 98-09-9 C6H5ClO2S 详情 详情
(VIII) 31439 ethyl 4-[3-methyl-5-[(phenylsulfonyl)amino]phenoxy]butanoate C19H23NO5S 详情 详情
(IX) 31441 4-[3-methyl-5-[(phenylsulfonyl)amino]phenoxy]butyric acid C17H19NO5S 详情 详情
(X) 31440 4-[3-methyl-5-[(phenylsulfonyl)amino]phenoxy]butanamide C17H20N2O4S 详情 详情
(XI) 31442 N-[3-(4-aminobutoxy)-5-methylphenyl]benzenesulfonamide C17H22N2O3S 详情 详情
(XII) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情

合成路线16

该中间体在本合成路线中的序号：(I)

Condensation of S-methylisothiourea (I) and cyano acetate derivative (II) by means of NaOMe in MeOH affords pyrimidine derivative (III), whose hydroxy group is converted into chloro by means of refluxing POCl3, yielding derivative (IV). Alkylation of (IV) with cyclopentylamine (V) and Et3N in CH2Cl2 provides derivative (VI), whose nitrile group is then reduced by means of LiAlH4 in THF to afford aminomethyl compound (VII). Treatment of (VII) with 1,1-carbonyldiimidazole (CDI) in refluxing THF gives pyrimidopyrimidinone (VIII), whose methylsulfanyl group is oxidized with 3-phenyl-2-(phenylsulfonyl)oxaziridine (IX) in CHCl3 to afford methyl sulfoxide derivative (X). Displacement of the methyl sulfoxide group of (X) with substituted aniline (XI) in TFA/acetonitrile yields 3,4-dihydropyrimidopyrimidinone (XII), which is finally oxidized by means of KOtBu in THF or DMSO.

参考文献 中间体
合成目标
【1】 Kramer, J.B.; et al.; Synthesis and biological activity of a novel series of pyrimidopyrimidinones as inhibitors of cyclin-dependent kinases. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 40.
【2】 Dobrusin, E.M.; Showalter, H.D.H.; Schroeder, M.C.; Toogood, P.; Kramer, J.B.; Trumpp-Kallmeyer, S.A.; Hamby, J.M. (Pfizer Inc.); Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation. WO 9961444 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IIa) 43041 ethyl (Z)-2-cyano-3-ethoxy-2-propenoate 94-05-3 C8H11NO3 详情 详情
(IIb) 43563 ethyl (E)-2-cyano-3-ethoxy-2-propenoate；(E)-ethyl 2-cyano-3-ethoxyacrylate 94-05-3 C8H11NO3 详情 详情
(I) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(III) 43555 4-hydroxy-2-(methylsulfanyl)-5-pyrimidinecarbonitrile C6H5N3OS 详情 详情
(IV) 43556 4-chloro-2-(methylsulfanyl)-5-pyrimidinecarbonitrile C6H4ClN3S 详情 详情
(V) 28850 cyclopentanamine 1003-03-8 C5H11N 详情 详情
(VI) 43557 4-(cyclopentylamino)-2-(methylsulfanyl)-5-pyrimidinecarbonitrile C11H14N4S 详情 详情
(VII) 43558 N-[5-(aminomethyl)-2-(methylsulfanyl)-4-pyrimidinyl]-N-cyclopentylamine; 5-(aminomethyl)-N-cyclopentyl-2-(methylsulfanyl)-4-pyrimidinamine C11H18N4S 详情 详情
(VIII) 43559 1-cyclopentyl-7-(methylsulfanyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one C12H16N4OS 详情 详情
(IX) 31834 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine;2-(Phenylsulfonyl)-3-phenyloxaziridine;2-Benzenesulfonyl-3-phenyloxaziridine;3-Phenyl-2-phenylsulfonyloxaziridine;3-Phenyl-N-phenylsulfonyloxaziridine;N-(Phenylsulfonyl)phenyloxaziridine;N-Benzenesulfonyl-3-phenyloxaziridine 63160-13-4 C13H11NO3S 详情 详情
(X) 43560 1-cyclopentyl-7-(methylsulfinyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one C12H16N4O2S 详情 详情
(XI) 43561 1-(4-aminophenyl)-4-piperidinol C11H16N2O 详情 详情
(XII) 43562 1-cyclopentyl-7-[4-(4-hydroxy-1-piperidinyl)anilino]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one C22H28N6O2 详情 详情

合成路线17

该中间体在本合成路线中的序号：(II)

The condensation between 3-methoxybenzaldehyde (I), S-methylisothiourea (II) and ethyl cyanoacetate (III) in the presence of K2CO3 in hot EtOH leads to pyrimidine (IV). Subsequent chlorination of (IV) by means of POCl3 and dimethylaniline furnishes the 6-chloropyrimidine (V). Reaction of (V) with ethyl mercaptoacetate (VI) and potassium tert-butoxide gives rise to the thienopyrimidine (VII). The ethyl ester group of (VII) is then hydrolyzed to the carboxylic acid (VIII) employing LiOH. Finally, coupling of acid (VIII) with tert-butylamine by means of TBTU produces the target N-tert-butyl amide

参考文献 中间体
合成目标
【1】 Adang, A.E.P.; Gerritsma, G.G.; Van Straten, N.C.R. (Akzo Nobel N.V.); Bicyclic heteroaromatic cpds. useful as LH agonists. EP 1171443; JP 2002541259; US 6569863; WO 0061586 .
【2】 Timmers, C.M.; Karstens, W.F.J. (Akzo Nobel N.V.); Bicyclic heteroaromatic cpds.. WO 0224703 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 20589 3-methoxybenzaldehyde; m-Anisaldehyde 591-31-1 C8H8O2 详情 详情
(II) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(III) 11877 Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate 105-56-6 C5H7NO2 详情 详情
(IV) 60410 4-hydroxy-6-(3-methoxyphenyl)-2-(methylsulfanyl)-5-pyrimidinecarbonitrile C13H11N3O2S 详情 详情
(V) 60411 4-chloro-6-(3-methoxyphenyl)-2-(methylsulfanyl)-5-pyrimidinecarbonitrile C13H10ClN3OS 详情 详情
(VI) 23995 ethyl 2-sulfanylacetate 2713-34-0 C4H8O2S 详情 详情
(VII) 60412 ethyl 5-amino-4-(3-methoxyphenyl)-2-(methylsulfanyl)thieno[2,3-d]pyrimidine-6-carboxylate C17H17N3O3S2 详情 详情
(VIII) 60413 5-amino-4-(3-methoxyphenyl)-2-(methylsulfanyl)thieno[2,3-d]pyrimidine-6-carboxylic acid C15H13N3O3S2 详情 详情

合成路线18

该中间体在本合成路线中的序号：(VI)

The Friedel Krafts reaction of fluorobenzene (I) and 3-nitro-4-chlorobenzoyl chloride (II) by means of AlCl3 gives 3-nitro-4-chloro-4’-fluorobenzophenone (III), which by reaction with NH3 in ethylenglycol at 130 C yields 3-nitro-4-amino-4’-fluorobenzophenone (IV). The reduction of (IV) with H2 over Pd/C in methanol affords 3,4-diamino-4’-fluorobenzophenone (V), which is finally cyclized with S-methylthiourea (VI) and methyl chloroformate by means of NaOH in water

参考文献 中间体
合成目标
【1】 Tan, K.; Duquette, M.; Liu, J.H.; Dong, Y.; Zhang, R.; Joachimiak, A.; Lawler, J.; Wang, J.H.; Crystal structure of the TSP-1 type 1 repeats: A novel layered fold and its biological implication. Arzneim-Forsch Drug Res 1978, 28, 4, 586.
【2】 Van Gelder, J.L.H.; et al. (Janssen Pharmaceutica NV); BE 752089; DE 2029637; FR 2052988; GB 1307306; US 3657267; ZA 7004191 .
【3】 Castaner, J.; Bogan, J.A.; Flubendazole.. Drugs Fut 1978, 3, 10, 739.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 17466 Fluorobenzene 462-06-6 C6H5F 详情 详情
(II) 14486 4-Chloro-3-nitrobenzoylchloride; 4-chloro-3-nitrobenzoyl chloride 38818-50-7 C7H3Cl2NO3 详情 详情
(III) 60714 (4-chloro-3-nitrophenyl)(4-fluorophenyl)methanone C13H7ClFNO3 详情 详情
(IV) 60715 (4-amino-3-nitrophenyl)(4-fluorophenyl)methanone C13H9FN2O3 详情 详情
(V) 60716 (3,4-diaminophenyl)(4-fluorophenyl)methanone C13H11FN2O 详情 详情
(VI) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情

合成路线19

该中间体在本合成路线中的序号：(V)

The condensation of 2-(chloromethyl)-1,4-dioxaspiro[4,5]decane (I) with the sodium salt of phthalimide (II) in hot DMF affords the N-substituted phthalimide (III). Subsequent phthaloyl group hydrazinolysis gives the primary amine (IV). Finally, condensation of amine (IV) with S-methyl pseudothiourea sulfate (V) leads to the title guanidine derivative

参考文献 中间体
合成目标
【1】 Aaron, J.E. Jr.; Hardie, W.R.; Process for the preparation of 1,3-dioxolan-4-yl-alcoyl-guanidines and its intermediates. FR 1522153 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 62349 2-(chloromethyl)-1,4-dioxaspiro[4.5]decane C9H15ClO2 详情 详情
(II) 12376 Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione 85-41-6 C8H5NO2 详情 详情
(III) 62350 2-(1,4-dioxaspiro[4.5]dec-2-ylmethyl)-1H-isoindole-1,3(2H)-dione C17H19NO4 详情 详情
(IV) 62351 1,4-dioxaspiro[4.5]dec-2-ylmethanamine; 1,4-dioxaspiro[4.5]dec-2-ylmethylamine C9H17NO2 详情 详情
(V) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情

合成路线20

该中间体在本合成路线中的序号：(VIII)

The reaction of 4-chloro-2-amino-1-nitrobenzene (I) with sodium phenylmercaptide (A) in DMF gives 2-amino-4-phenylthio-1-nitrobenzene (II), which is treated with acetic anhydride to yield 2-acetamido-4-phenylthio-1-nitrobenzene (III). This product is oxidized with peracetic acid in methanol giving 2-amino-4-phenylsulfinyl-1-nitrobenzene (V). Then the nitro group is reduced with H2 over Pd/C in methanol yielding 1,2-diamino-4-phenylsulfinylbenzene (VI). This product is finally condensed with N,N'-bis(methoxycarbonyl)-S-methylisothiourea (VII) in ethanol - water - acetic acid. The isothiourea (VII) is obtained by reaction of S-methylisothiouronium sulfate (VIII) with methyl chloroformate (B) by means of KOH in water

参考文献 中间体
合成目标
【1】 Beard, C.C.; et al. (Syntex, Inc.); DE 2363351 .
【2】 Castaner, J.; Bogan, J.A.; Oxfendazole. Drugs Fut 1976, 1, 9, 438.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 16993 methyl chlorocarbonate;Carbonochloridic acid methyl ester；[(chlorocarbonyl)oxy]methane；methyl chloroformate 79-22-1 C2H3ClO2 详情 详情
(A) 60753 sodium benzenethiolate C6H5NaS 详情 详情
(I) 15709 5-chloro-2-nitrophenylamine; 5-chloro-2-nitroaniline 1635-61-6 C6H5ClN2O2 详情 详情
(II) 60754 2-nitro-5-(phenylsulfanyl)aniline; 2-nitro-5-(phenylsulfanyl)phenylamine C12H10N2O2S 详情 详情
(III) 60755 N-[2-nitro-5-(phenylsulfanyl)phenyl]acetamide C14H12N2O3S 详情 详情
(IV) 60756 N-[2-nitro-5-(phenylsulfinyl)phenyl]acetamide C14H12N2O4S 详情 详情
(V) 60757 2-nitro-5-(phenylsulfinyl)aniline; 2-nitro-5-(phenylsulfinyl)phenylamine C12H10N2O3S 详情 详情
(VI) 60758 4-(phenylsulfinyl)-1,2-benzenediamine; 2-amino-4-(phenylsulfinyl)phenylamine C12H12N2OS 详情 详情
(VII) 28696 methyl (Z)-[(methoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate C6H10N2O4S 详情 详情
(VIII) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
Extended Information