Yaozh News Star Club Edu BBS TOP100 Customer Service APP
Iphone Download Android Download
  • English
  • 简体中文
Login Register
Search
Current Location： Home > Feedback Help Print

【结 构 式】

【分子编号】12849

【品名】Nicotinaldehyde; 3-Pyridinecarboxaldehyde

【CA登记号】500-22-1

【 分 子 式 】C6H5NO

【 分 子 量 】107.11184

【元素组成】C 67.28% H 4.71% N 13.08% O 14.94%
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：(II)

The cyclization of pyridine-3-carbaldehyde (II) with L-cysteine (I) in ethanol gives the thiazolidine derivative (III), which is treated with formic acid yielding the 3-formylthiazolidine derivative (IV). The cyclization of (IV) with 2-chloropropenenitrile (V) by means of acetic anhydride affords 3-(3-pyridil)-1H,3H-pyrrolo[1,2-c]thiazole-7-carbonitrile (VI), which is finally hydrolyzed to the target carboxamide by means of KOH in tert-butanol.

参考文献 中间体
合成目标
【1】 Fabre, J.-L.; Farge, D.; James, C.; Lavé, D. (Aventis SA); Novel 1H,3H-pyrrolo[1,2-c]thiazole derivs., their preparation and medicaments containing them. EP 0115979; US 4529728 .
【2】 Lavé, D.; James, C.; Rajoharison, H.; Bost, P.E.; Cavero, I.; PYRROLO[1,2-c]THIAZOLE DERIVATIVES: POTENT PAF RECEPTOR ANTAGONISTS. Drugs Fut 1989, 14, 9, 891.
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) 14643 L-cysteine; (R)-2-Amino-3-mercaptopropionic acid 52-90-4 C3H7NO2S 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 38634 (4R)-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid C9H10N2O2S 详情 详情
(IV) 43711 (4R)-3-formyl-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid C10H10N2O3S 详情 详情
(V) 12372 2-Chloroacrylonitrile 920-37-6 C3H2ClN 详情 详情
(VI) 43712 3-(3-pyridinyl)-1H-pyrrolo[1,2-c][1,3]thiazole-7-carbonitrile C12H9N3S 详情 详情

合成路线2

该中间体在本合成路线中的序号：(I)

Grignard reaction of 3-trifluoromethylbenzene-magnesium bromide (II) with 3-pyridinecarboxaldehyde (I) in THF at 15 C gives alpha-[3-(trifluoromethyl)phenyl]-3-pyridinemethanol (III). Oxidation of this compound with MnO2 in refluxing CH2Cl2 yields the corresponding ketone (IV). The oximation reaction carried out with NH2OH.HCl in isopropanol-HCl at 70 C affords (3-pyridinyl)-[3-(trifluoromethyl)phenyl]methanone oxime (V) (more than 90% of the E-isomer). The alkylation of (V) with ethyl bromovalerate in the presence of NaOH in DMF produces ethyl 5-[[[(3-pyridinyl)[3-(trifluoromethyl)phenyl]methylene]amino]oxy] pentanoate (VI). Hydrolysis of the ester with aqueous NaOH followed by HCl treatment gives, after recrystallization from diisopropylether, ridogrel.

参考文献 中间体
合成目标
【1】 Freyne, E.J.E.; Raeymaekers, A.H.; Sipido, V.; Venet, M.G. (Janssen Pharmaceutica NV); Pharmaceutical use of [[[(3-pyridinyl)methylen]amino]oxy]alkanoic acid and esters. EP 0221601; JP 1987161759; JP 1991068556; US 4746671 .
【2】 Freyne, E.J.; Raeymaekers, A.H.M.; Venet, M.G.; Sipido, V.K.; De Clerck, F.; RIDOGREL. Drugs Fut 1990, 15, 5, 463.
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) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(II) 12028 Bromo[3-(trifluoromethyl)phenyl]magnesium 402-26-6 C7H4BrF3Mg 详情 详情
(III) 12029 3-Pyridinyl[3-(trifluoromethyl)phenyl]methanol C13H10F3NO 详情 详情
(IV) 12030 3-Pyridinyl[3-(trifluoromethyl)phenyl]methanone C13H8F3NO 详情 详情
(V) 12031 3-Pyridinyl[3-(trifluoromethyl)phenyl]methanone oxime C13H9F3N2O 详情 详情

合成路线3

该中间体在本合成路线中的序号：(II)

The cyclization of pyridine-3-carbaldehyde (II) with L-cysteine (I) in ethanol gives the thiazolidine derivative (III), which is treated with formic acid, yielding a diastereomeric mixture of formyl derivatives from which the desired (2R,4R)-(IV) is isolated by crystallization. The cyclization of (2R,4R)-(IV) with ethyl 2,3-dichloropropionate (V) by means of TsCl and Et3N affords (2R)-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxylic acid ethyl ester (VI), which is hydrolyzed with NaOH to the corresponding free acid (VII). Finally, this compound is condensed with 3-aminobenzophenone (VIII) by means of SOCl2 to provide the target amide.

参考文献 中间体
合成目标
【1】 (Aventis SA); 1H,3H-pyrrolo[1,2-c]thiazole derivs.. EP 0253711; FR 2601015; JP 1988022589 .
【2】 Rajoharison, H.G. (Aventis Pharma SA); Process for the preparation of dextrorotatory 3-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]-7-thiazolecarboxylic acid. EP 0297987; US 4906757 .
【3】 Lavé, D.; James, C.; Rajoharison, H.; Bost, P.E.; Cavero, I.; PYRROLO[1,2-c]THIAZOLE DERIVATIVES: POTENT PAF RECEPTOR ANTAGONISTS. Drugs Fut 1989, 14, 9, 891.
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) 14643 L-cysteine; (R)-2-Amino-3-mercaptopropionic acid 52-90-4 C3H7NO2S 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 38634 (4R)-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid C9H10N2O2S 详情 详情
(IV) 43713 (2R,4R)-3-formyl-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid C10H10N2O3S 详情 详情
(V) 43714 ethyl 2,3-dichloropropanoate 6628-21-3 C5H8Cl2O2 详情 详情
(VI) 43715 ethyl (3R)-3-(3-pyridinyl)-1H-pyrrolo[1,2-c][1,3]thiazole-7-carboxylate C14H14N2O2S 详情 详情
(VII) 43716 (3R)-3-(3-pyridinyl)-1H-pyrrolo[1,2-c][1,3]thiazole-7-carboxylic acid C12H10N2O2S 详情 详情
(VIII) 39112 3-Aminobenzophenone; (3-aminophenyl)(phenyl)methanone 2835-78-1 C13H11NO 详情 详情

合成路线4

该中间体在本合成路线中的序号：(II)

Milameline can be obtained by three related ways: 1) By reaction of 1-methyl-1,2,3,6-tetrahydropyridine-3-carbaldehyde (I) with methoxyamine by means of triethylamine in DMF. 2) The reaction of pyridine-3-carbaldehyde (II) with methoxyamine in refluxing methanol gives the corresponding oxime (III), which is alkylated with methyl iodide in refluxing ethyl acetate yielding 3-(methoxyiminomethyl)-1-methylpyridinium iodide (IV). Finally, this compound is hydrogenated with NaBH4 in methanol/water. 3) The reaction of 1,2,3,6-tetrahydropyridine-3-carbaldehyde (V) with methoxyamine gives the corresponding oxime (VI), which is then alkylated with methyl iodide in DMF.

参考文献 中间体
合成目标
【1】 Souda, S.; Ueda, N.; Miyazawa, S.; Tagami, K.; Nomoto, S.; Okita, M.; Shimomura, N.; Kaneko, T.; Fujimoto, M.; Murakami, M.; Oketani, K.; Fujisaki, H.; Shibata, H.; Wakabayashi, T. (Eisai Co., Ltd.); Pyridine derivs., pharmaceutical compsns. comprising the same, the use of the same for the manufacture of medicaments having therapeutic or preventative value, and a process for preparing the same. AU 8781138; EP 0268956; EP 0475456; EP 0654471; EP 0786461; JP 1989006270; JP 1993247035; JP 1995291967; US 5045552; US 5998445 .
【2】 Graul, A.; Castaner, J.; Milameline Hydrochloride. Drugs Fut 1996, 21, 11, 1124.
【3】 Bergmeier, S.C.; Downs, D.A.; Moos, W.H.; Moreland, D.W.; Tecle, H. (Pfizer Inc.); O-Substd. tetrahydropyridine oxime cholinergic agents. AU 8781102; EP 0271798; JP 1988215664; US 4710508 .
【4】 Galliani, G.; Barzaghi, F.; Butti, A.; Bonetti, C.; Toja, E. (Aventis Pharma SA); 1,2,5,6-Tetrahydropyridine-3-carboxaldehyde oxime derivs., process for their preparation, their application as medicaments and compsns. containing them. EP 0239445; JP 1987252767; US 5219872 .
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) 12848 1-Methyl-1,2,5,6-tetrahydro-3-pyridinecarbaldehyde C7H11NO 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 12850 Nicotinaldehyde O-methyloxime C7H8N2O 详情 详情
(IV) 12851 3-[(Methoxyimino)methyl]-1-methylpyridinium iodide C8H11IN2O 详情 详情
(V) 12852 1,2,5,6-Tetrahydro-3-pyridinecarbaldehyde C6H9NO 详情 详情
(VI) 12853 1,2,5,6-Tetrahydro-3-pyridinecarbaldehyde O-methyloxime C7H12N2O 详情 详情

合成路线5

该中间体在本合成路线中的序号：(A)

Pyridine-3-carboxaldehyde O-methyloxime (I) is prepared either by methylation of 3-pyridinealdoxime sodium salt or by condensation of 3-pyridinecarboxaldehyde with methoxylamine in water. Quaternization of (I) with ethyl iodide gives 3-(methoxyiminomethyl)-1-ethylpyridinium iodide (II), which is reduced by means of sodium borohydride in methanol to 1-ethyl-1,2,5,6-tetrahydropyridine-3-carboxaldehyde O-methyloxime (III). Cleavage of the ethyl group is obtained by reaction with 4-chlorophenylchloroformate in refluxing dichloroethane to yield RU 47213. Ru 47213 is obtained as pure (E)-isomer. Under UV irradiation in toluene it is partially converted into the sterically unfavored (Z)-isomer.

参考文献 中间体
合成目标
【1】 Barzaghi, F.; Galliani, G.; Toja, E.; RU 47213. Drugs Fut 1994, 19, 5, 454.
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) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(D) 16170 1,2-dichloroethane 107-06-2 C2H4Cl2 详情 详情
(B) 31260 nicotinaldehyde oxime 1193-92-6 C6H6N2O 详情 详情
(I) 12850 Nicotinaldehyde O-methyloxime C7H8N2O 详情 详情
(II) 31259 1-ethyl-3-[(methoxyimino)methyl]pyridinium iodide C9H13IN2O 详情 详情
(III) 31261 1-ethyl-1,2,5,6-tetrahydro-3-pyridinecarbaldehyde O-methyloxime C9H16N2O 详情 详情
(C) 17779 1-chloro-4-[(chlorocarbonyl)oxy]benzene 7693-45-0 C7H4Cl2O2 详情 详情

合成路线6

该中间体在本合成路线中的序号：(I)

The cyclization of pyridine-3-carbaldehyde (I) with L-cysteine (II) gives 2-(3-pyridyl)thiazolidine-4(R)-carboxylic acid (II), which is finally condensed with 1-(3-phenylpropyl)piperazine (IV) by means of DCC and HOBT in DMF. The intermediate 1-(3-phenylpropyl)piperazine (IV) has been obtained as follows: The condensation of piperazine-1-carboxylic acid ethyl ester (V) with 3-phenylpropyl bromide (VI) by means of K2CO3 in 2-butanone gives 4-(3-phenylpropyl)piperazine-1-carboxylic acid ethyl ester (VII), which is decarboxylated with NaOH in refluxing ethanol.

参考文献 中间体
合成目标
【1】 Mase, T.; Hara, H.; Nagaoka, H.; Takahasi, T.; Suzuki, T.; Tomioka, K.; Yamada, T. (Yamanouchi Pharmaceutical Co., Ltd.); Saturated heterocyclic carboxamide derivs.. AU 8812080; EP 0279681; JP 1988208582; US 4987132 .
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) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(II) 38633 (2S)-2-amino-2-(methylsulfanyl)ethanoic acid C3H7NO2S 详情 详情
(III) 38634 (4R)-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid C9H10N2O2S 详情 详情
(IV) 38636 1-(3-phenylpropyl)piperazine C13H20N2 详情 详情
(V) 24694 N-ethoxycarbonylpiperidine; Ethyl 1-piperazinecarboxylate; N-Ethoxycarbonyl piperazine; N-Carbethoxy piperazine 120-43-4 C7H14N2O2 详情 详情
(VI) 20884 1-(3-bromopropyl)benzene 637-59-2 C9H11Br 详情 详情
(VII) 38635 ethyl 4-(3-phenylpropyl)-1-piperazinecarboxylate C16H24N2O2 详情 详情

合成路线7

该中间体在本合成路线中的序号：(I)

The cyclization of pyridine-3-carbaldehyde (I) with L-cysteine (II) gives 2-(3-pyridyl)thiazolidine-4(R)-carboxylic acid (III), which is finally condensed with 1-(3-methyl-3-phenylbutyl)piperazine (IV) by means of DCC and HOBT In DMF. The intermediate 1-(3-methyl-3-phenylbutyl)piperazine (IV) has been obtained as follows: The reduction of 3-methyl-3-phenylbutyric acid (IV) with LiAlH4 in THF gives the corresponding butanol (V), which is treated with refluxing 48% HBr to yield the 3-methyl-3-phenylbutyl bromide (VI). The condensation of (VI) with piperazine-1-carboxylic acid ethyl ester (VII) by means of K2CO3 in 2-butanone gives 4-(3-methyl-3-phenylbutyl)piperazine-1-carboxylic acid ethyl ester (VIII), which is decarboxylated with NaOH in refluxing ethanol.

参考文献 中间体
合成目标
【1】 Mase, T.; Hara, H.; Nagaoka, H.; Takahasi, T.; Suzuki, T.; Tomioka, K.; Yamada, T. (Yamanouchi Pharmaceutical Co., Ltd.); Saturated heterocyclic carboxamide derivs.. AU 8812080; EP 0279681; JP 1988208582; US 4987132 .
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) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(II) 38633 (2S)-2-amino-2-(methylsulfanyl)ethanoic acid C3H7NO2S 详情 详情
(III) 38634 (4R)-2-(3-pyridinyl)-1,3-thiazolidine-4-carboxylic acid C9H10N2O2S 详情 详情
(IV) 38637 3-methyl-3-phenylbutyric acid C11H14O2 详情 详情
(IV) 38641 1-(3-methyl-3-phenylbutyl)piperazine C15H24N2 详情 详情
(V) 38638 3-methyl-3-phenyl-1-butanol C11H16O 详情 详情
(VI) 38639 1-(3-bromo-1,1-dimethylpropyl)benzene C11H15Br 详情 详情
(VII) 24694 N-ethoxycarbonylpiperidine; Ethyl 1-piperazinecarboxylate; N-Ethoxycarbonyl piperazine; N-Carbethoxy piperazine 120-43-4 C7H14N2O2 详情 详情
(VIII) 38640 ethyl 4-(3-methyl-3-phenylbutyl)-1-piperazinecarboxylate C18H28N2O2 详情 详情

合成路线8

该中间体在本合成路线中的序号：(II)

SR 27417 (N-(2-dimethylaminoethyl)-N-(3-pyridinylmethyl)[4-(2,4,6-triisopropylphenyl)thiazol-2-yl]amine difumarate) was prepared via a convergent route. Reductive amination of N,N-dimethylaminoethanamine (I) and pyridyl-3-carboxaldehyde (II) by sodium borohydride gave the amine (III). Eaction of pivaloyl chloride (IV) and potassium thiocyanate in anhydrous acetone provided the pivaloyl isothiocyanate (V), which was condensed in situ with the amine (III) to afford the protected thiourea (VI). Chlorhydric hydrolysis of (IV) gave the thiourea (VII) with the bromoketene (IX) in refluxing ethanol led to SR 27417.

参考文献 中间体
合成目标
【1】 Herbert, J.M.; Valette, G.; Bernat, A.; Savi, P.; Maffrand, J.P.; Le Fur, G.; SR 27417, a highly potent, selective and long-acting antagonist of the PAF receptor. Drugs Fut 1992, 17, 11, 1011.
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) 14881 N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine 108-00-9 C4H12N2 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 14883 N-[2-(dimethylamino)ethyl]-N-(3-pyridinylmethyl)amine; N(1),N(1)-dimethyl-N(2)-(3-pyridinylmethyl)-1,2-ethanediamine C10H17N3 详情 详情
(IV) 13597 2,2-Dimethylpropanoyl chloride; Pivaloyl chloride 3282-30-2 C5H9ClO 详情 详情
(V) 14885 2,2-dimethylpropanoyl isothiocyanate C6H9NOS 详情 详情
(VI) 14886 N-[2-(dimethylamino)ethyl]-N'-(2,2-dimethylpropanoyl)-N-(3-pyridinylmethyl)thiourea C16H26N4OS 详情 详情
(VII) 14887 N-[2-(dimethylamino)ethyl]-N-(3-pyridinylmethyl)thiourea C11H18N4S 详情 详情
(VIII) 14888 1,3,5-triisopropylbenzene 717-74-8 C15H24 详情 详情
(IX) 14889 2-bromo-1-(2,4,6-triisopropylphenyl)-1-ethanone C17H25BrO 详情 详情

合成路线9

该中间体在本合成路线中的序号：(I)

BCX-34 is synthesized from 3-pyridylcarboxaldehyde in ten steps in 10% overall yield as described by Montgomery et al. and depicted in Scheme 19337601a. The reaction of (I) with cyanoacetic acid followed by sodium borohydride reduction of the substituted acrylonitrile intermediate gave (II) in good yield. A key step in the synthesis is the formation of aldehyde (III) using sodium hydride and ethyl formate. The enamine (IV) is then prepared from (III) and glycine methyl ester hydrochloride buffered with sodium acetate. Protection of the enamine nitrogen of (IV) is required to yield (V) before cyclization to pyrrole (VI) is carried out using 1,5-diazabicyclo[4.3.0]non-5-ene (DBN). This reaction gives a mixture of (VI) and (VII) as products and the mixture is all converted to (VII) by sodium carbonate hydrolysis before isolation of solid (VII). The cyclization of the pyrimidine ring portion of BCX-34 is accomplished in three steps from (VII) through a sequence first described by Yamazaki et al. A study of the reaction conditions for the final cyclization step of the synthesis of Peldesine described in scheme 19337601a, in order to improve the yield of the target compound, and to minimize the side products, is presented in Org Proc Res Develop 2000, 4: 129.

参考文献 中间体
合成目标
【1】 Yamazaki, A.; Takenishi, T.; Kumashiro, L.; Synthesis of guanosine and its derivatives from 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide. I. Ring closure with benzoyl isothiocyanate. J Org Chem 1967, 32, 1825-8.
【2】 Pathak, V.P.; Selective formation of pyrrolo[3,2-d]pyrimidines from methyl[(N-benzoyl-S-methylisothiocarbamoyl)amino]-1H-pyrrole-2-carboxylate. Org Process Res Dev 2000, 4, 2, 129.
【3】 Niwas, S.; Secrist, J.A. III, Babu, Y.S.; Ealick, S.E.; Montgomery, J.A.; Guida, W.C.; Bugg, C.E.; Rose, J.D.; Erion, M.D.; Structure-based design of inhibitors of purine nucleoside phosphorylase. 1. 9-(Arylmethyl) derivatives of 9-deazaguanine. J Med Chem 1993, 36, 1, 55-9.
【4】 Walsh, D.A.; Walsh, G.M.; Montgomery, J.A.; Snyder, H.W. Jr.; BCX-34. Drugs Fut 1993, 18, 10, 887.
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) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(II) 16026 3-(3-pyridinyl)propanenitrile C8H8N2 详情 详情
(III) 16027 2-formyl-3-(3-pyridinyl)propanenitrile C9H8N2O 详情 详情
(IV) 16028 methyl 2-[[(Z)-2-cyano-3-(3-pyridinyl)-1-propenyl]amino]acetate C12H13N3O2 详情 详情
(V) 16029 methyl 2-[[(Z)-2-cyano-3-(3-pyridinyl)-1-propenyl](ethoxycarbonyl)amino]acetate C15H17N3O4 详情 详情
(VI) 16030 methyl 3-amino-4-(3-pyridinylmethyl)-1H-pyrrole-2-carboxylate C12H13N3O2 详情 详情
(VII) 16031 1-ethyl 2-methyl 3-amino-4-(3-pyridinylmethyl)-1H-pyrrole-1,2-dicarboxylate C15H17N3O4 详情 详情
(VIII) 16032 methyl 3-[[(benzoylamino)carbothioyl]amino]-4-(3-pyridinylmethyl)-1H-pyrrole-2-carboxylate C20H18N4O3S 详情 详情
(IX) 16033 methyl 3-[[(Z)-(benzoylamino)(methylsulfanyl)methylidene]amino]-4-(3-pyridinylmethyl)-1H-pyrrole-2-carboxylate C21H20N4O3S 详情 详情

合成路线10

该中间体在本合成路线中的序号：(I)

The reaction of pyridine-3-carbaldehyde (I) with KCN in acetic acid, followed by a treatment with NH4Cl in aqueous NH4OH yields 2-amino-2-(3-pyridyl)acetonitrile (II), which is cyclized to 3-chloro-4-(3-pyridyl)-1,2,5-thiadiazole (III) by a treatment with S2Cl2 in DMF. The reaction of (III) with sodium hexyloxide in hexanol yields 3-(hexyloxy)-4-(3-pyridyl)-1,2,5-thiadiazole (IV), which is treated with methyl iodide in acetone to afford the corresponding N-methylpyridinium salt (V). Finally, this compound is hydrogenated with NaBH4 in ethanol and salified with oxalic or L-tartaric acid in acetone or isopropanol.

参考文献 中间体
合成目标
【1】 Graul, A.; Castaner, J.; Xanomeline. Drugs Fut 1996, 21, 9, 911.
【2】 Sauerberg, P.; Olesen, P.H. (Ferrosan A/S); Piperidine cpds. and their preparation and use. EP 0384288; US 5260311; US 5264444; US 5328925 .
【3】 Sauerberg, P.; Olesen, P.H.; Mitch, c.H. (Novo Nordisk A/S); Heterocyclic cpds. and their preparation and use. EP 0687265; JP 1996507298; WO 9420495 .
【4】 Osborne, L.M.; Shipley, L.A.; Treppendahl, S.; Petersen, T.G. (Novo Nordisk A/S); Heterocyclic chemistry. US 5834495; WO 9429303 .
【5】 Sauerberg, P.; Olesen, P.H.; Nielsen, S.; et al.; Novel functional M1selective muscarinic agonists. Synthesis and structure-activity relationships of 3-(1,2,5-thiadiazolyl)-1,2,5,6-tetrahydro-1-methylpyridines. J Med Chem 1992, 35, 12, 2274-83.
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) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(II) 16175 2-amino-2-(3-pyridinyl)acetonitrile C7H7N3 详情 详情
(III) 16176 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine C7H4ClN3S 详情 详情
(IV) 16177 3-[4-(hexyloxy)-1,2,5-thiadiazol-3-yl]pyridine; hexyl 4-(3-pyridinyl)-1,2,5-thiadiazol-3-yl ether C13H17N3OS 详情 详情
(V) 16178 3-[4-(hexyloxy)-1,2,5-thiadiazol-3-yl]-1-methylpyridinium iodide C14H20IN3OS 详情 详情

合成路线11

该中间体在本合成路线中的序号：(V)

Methylation of methyl (+)-lactate (I) followed by thioacetylation and acidic hydrolysis affords (-)-thiolactic acid (IV). Reaction of 3-pyridinecarboxyaldehyde (V) with methylamine in toluene under the azeotropic condition provides the imine (VI), which when condensed with (IV) affords (+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one (VII). Treatment of (VII) with aqueous HCl/isopropanol results in the precipitation of SM-12502.

参考文献 中间体
合成目标
【1】 Koike, H.; Natsume, Y.; Tojo, S.; Morooka, S.; SM-12502. Drugs Fut 1995, 20, 2, 153.
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) 11591 methyl (2R)-2-hydroxypropanoate 17392-83-5 C4H8O3 详情 详情
(II) 16679 methyl (2R)-2-[(methylsulfonyl)oxy]propanoate C5H10O5S 详情 详情
(III) 16680 methyl (2S)-2-(acetylsulfanyl)propanoate C6H10O3S 详情 详情
(IV) 16681 (2S)-2-sulfanylpropionic acid C3H6O2S 详情 详情
(V) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(VI) 16683 N-methyl-N-[(Z)-3-pyridinylmethylidene]amine; N-[(Z)-3-pyridinylmethylidene]methanamine C7H8N2 详情 详情
(VII) 16684 (2R,5S)-3,5-dimethyl-2-(3-pyridinyl)-1,3-thiazolan-4-one C10H12N2OS 详情 详情

合成路线12

该中间体在本合成路线中的序号：(I)

Knoevenagel condensation of pyridine-3-carboxaldehyde (I) with malonic acid in the presence of ammonium acetate afforded the racemic amino acid (III), which was acylated with phenylacetyl chloride (IV) to give amide (V). Optical resolution of (V) by means of penicillin amidase produced the hydrolysis of the undesired (R)-enantiomer. After isolation of the unreacted (S)-enantiomer (VI), its hydrolysis with aqueous HCl furnished the chiral amino acid (VII), which was converted to methyl ester (VIII) with 2,2-dimethoxypropane in MeOH. Coupling of (VIII) with N-Boc-(R)-nipecotic acid (IX) using 2-benzotriazolyl-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) provided amide (X). Deprotection of the Boc group of (X) was then achieved with HCl in dioxan resulting amine (XI).

参考文献 中间体
合成目标
【1】 Hoekstra, W.J.; Damiano, B.P.; Maryanoff, B.E.; et al.; Potent orally active GPIIb/IIIa antagonists containing a nipecotic acid subunit. Structure - Activity studies leading to the discovery of RWJ-53308. J Med Chem 1999, 42, 25, 5254.
【2】 Costanzo, M.J.; Hoekstra, W.J.; Maryanoff, B.E. (Ortho-McNeil Pharmaceutical, Inc.); Carboxamide derivs. of pyrrolidine, piperidine and hexahydroazepine for the treatment of thrombosis disorders. EP 0923555; JP 2000510111; US 6069254; WO 9741102 .
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) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(II) 12963 Malonic acid 141-82-2 C3H4O4 详情 详情
(III) 27468 3-(3-pyridinyl)-beta-alanine C8H10N2O2 详情 详情
(IV) 25890 2-phenylacetyl chloride；Phenylacetyl chloride;Phenacetyl chloride;Benzeneacetyl chloride 103-80-0 C8H7ClO 详情 详情
(V) 27469 N-(2-phenylacetyl)-3-(3-pyridinyl)-beta-alanine C16H16N2O3 详情 详情
(VI) 27470 (3S)-3-[(2-phenylacetyl)amino]-3-(3-pyridinyl)propionic acid C16H16N2O3 详情 详情
(VII) 27471 (3S)-3-amino-3-(3-pyridinyl)propionic acid C8H10N2O2 详情 详情
(VIII) 27472 methyl (3S)-3-amino-3-(3-pyridinyl)propanoate C9H12N2O2 详情 详情
(IX) 27473 (3R)-1-(tert-butoxycarbonyl)-3-piperidinecarboxylic acid C11H19NO4 详情 详情
(X) 27474 tert-butyl (3R)-3-([[(1S)-3-methoxy-3-oxo-1-(3-pyridinyl)propyl]amino]carbonyl)-1-piperidinecarboxylate C20H29N3O5 详情 详情
(XI) 27475 methyl (3S)-3-[[(3R)piperidinylcarbonyl]amino]-3-(3-pyridinyl)propanoate C15H21N3O3 详情 详情

合成路线13

该中间体在本合成路线中的序号：(V)

The cyclization of the amino group of 4-amino-3-(4-chlorophenyl)butyric acid (I) with 2,5-dimethoxytetrahydrofuran (II) by means of AcOH in THF gives the corresponding pyrrole (III), which is cyclized by means of TEA, ClCOOEt, pyrrolidine and POCl3 in toluene yielding the pyrrolopyridone (IV). Finally, this compound is condensed with pyridine-3-carbaldehyde (V) by means of tetrabutylammonium bisulfate and NaOH in water.

参考文献 中间体
合成目标
【1】 Moslemi, S.; Dallemagne, P.; Enguehard, C.; Sonnet, P.; Séralini, G.-E.; Bureau, R.; Auvray, P.; Sourdaine, P.; Guillon, J.; Rault, S.; MR 20492 and MR 20494: Two indolizinone derivatives that strongly inhibit human aromatase. J Steroid Biochem Mol Biol 1999, 70, 1-3, 59.
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) 36490 4-amino-3-(4-chlorophenyl)butyric acid 1134-47-0 C10H12ClNO2 详情 详情
(II) 12132 2,5-Dimethoxytetrahydrofuran; 5-Methoxytetrahydro-2-furanyl methyl ether 696-59-3 C6H12O3 详情 详情
(III) 36491 3-(4-chlorophenyl)-4-(1H-pyrrol-1-yl)butyric acid C14H14ClNO2 详情 详情
(IV) 18742 6-(4-chlorophenyl)-6,7-dihydro-8(5H)-indolizinone C14H12ClNO 详情 详情
(V) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情

合成路线14

该中间体在本合成路线中的序号：(II)

Aldol condensation of 3-pyridinecarboxaldehyde (II) with tetralone (I) in the presence of piperidine provided unsaturated ketone (III). This was subjected to reductive amination with ammonium formate and sodium cyanoborohydride to give the cis-aminotetralin (IV). Finally, amine (IV) was coupled with [4-(2-oxo-1-benzimidazolinyl)piperidin-1-yl]acetic acid (V) using HBTU.

参考文献 中间体
合成目标
【1】 Lovenberg, T.W.; Dax, S.L.; McNally, J.J.; Wilson, S.; Nepomuceno, D.; Youngman, M.A.; N-acylated alpha-(3-pyridylmethyl)-beta-aminotetralin antagonists of the human neuropeptide Y Y5 receptor. Bioorg Med Chem Lett 2000, 10, 15, 1641.
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) 40937 6-hydroxy-3,4-dihydro-2(1H)-naphthalenone C10H10O2 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 44719 6-hydroxy-1-[(Z)-3-pyridinylmethylidene]-3,4-dihydro-2-naphthalenone C16H13NO2 详情 详情
(IV) 44720 (5R,6S)-6-amino-5-(3-pyridinylmethyl)-5,6,7,8-tetrahydro-2-naphthalenol C16H18N2O 详情 详情
(V) 44721 2-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]acetic acid C14H17N3O3 详情 详情

合成路线15

该中间体在本合成路线中的序号：(I)

The condensation of 3-pyridincarboxaldehyde (I) with diethyl malonate (II) by means of piperidine in refluxing benzene gives diethyl (3-pyridyl)methylenemalonate (III), which by reaction with dimethylamine (A) in ether is converted into diethyl alpha-dimethylamino-(3-pyridyl)methylmalonate (IV). The reduction of (IV) with LiAlH4 in THF affords 2-[alpha-dimethylamino-(3-pyridyl)methyl]-1,3-propanediol (V), which is finally cyclized with paraformaldehyde by means of boron trifluoride ethearate in acetonitrile. (1-3)

参考文献 中间体
合成目标
【1】 Booher, R.N. (Eli Lilly and Company); US 3905987 .
【2】 Blancafort, P.; Serradell, M.N.; Castaner, J.; Doxpicomine hydrochloride. Drugs Fut 1981, 6, 9, 548.
【3】 Booher, R.N.; et al.; Various 5-substituted and 2,5-disubstituted 1,3-dioxanes, a new class of analgesic agents. J Med Chem 1977, 20, 7, 885.
【4】 Booher, R.N. (Eli Lilly and Company); US 3962269 .
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) 19443 N-methylmethanamine; N,N-dimethylamine 124-40-3 C2H7N 详情 详情
(I) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(II) 16829 Diethyl malonate 105-53-3 C7H12O4 详情 详情
(III) 60974 diethyl 2-(3-pyridinylmethylene)malonate C13H15NO4 详情 详情
(IV) 60975 diethyl 2-[(dimethylamino)(3-pyridinyl)methyl]malonate C15H22N2O4 详情 详情
(V) 60976 2-[(dimethylamino)(3-pyridinyl)methyl]-1,3-propanediol C11H18N2O2 详情 详情

合成路线16

该中间体在本合成路线中的序号：(II)

The reductive alkylation of 4-(2-methoxyphenoxy)aniline (I) with pyridine-3-carboxaldehyde (II) in the presence of NaBH4 leads to the N-pyridylmethyl aniline adduct (III) (1). Alternatively, 4-bromoaniline (IV) is reductively alkylated with pyridine-3-carboxaldehyde (II) to produce (V). Subsequent copper-catalyzed bromide displacement of (V) with guaiacol (VI) affords intermediate (III) (2). Finally, acylation of amine (III) with 2,2,2-trifluoroethylsulfonyl chloride (VII) gives rise to the target sulfonamide (1,2).

参考文献 中间体
合成目标
【1】 Johnson, M.P.; Baez, M.; Jagdmann, G.E.Jr.; Britton, T.C.; Large, T.H.; Callagaro, D.O.; Tizzano, J.P.; Monn, J.A.; Schoepp, D.D.; Discovery of allosteric potentiators for the metabotropic glutamate 2 receptor: Synthesis and subtype selectivity of N-(4-(2-methoxyphenoxy)phenyl)-N-(2,2,2-trifluoroethylsulfonyl)pyrid-3-ylmethylamine. J Med Chem 2003, 46, 15, 3189.
【2】 Monn, J.A.; Hornback, W.J.; Schoepp, D.D.; Dressman, B.A.; Britton, T.C.; Tizzano, J.P.; Johnson, K.W.; Henry, S.S.; Coleman, D.S.; Jagdmann, G.E.J.; Johnson, M.P.; Large, T.H.; Barda, D.A.; Fichtner, M.W. (Eli Lilly and Company); Potentiators of glutamate receptors. WO 0156990 .
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) 65013 4-{[2-(methyloxy)phenyl]oxy}aniline; 4-{[2-(methyloxy)phenyl]oxy}phenylamine C13H13NO2 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 65014 N-(4-{[2-(methyloxy)phenyl]oxy}phenyl)-N-(3-pyridinylmethyl)amine; 4-{[2-(methyloxy)phenyl]oxy}-N-(3-pyridinylmethyl)aniline C19H18N2O2 详情 详情
(IV) 22531 4-Bromoaniline; 4-Bromophenylamine 106-40-1 C6H6BrN 详情 详情
(V) 65015 4-bromo-N-(3-pyridinylmethyl)aniline; N-(4-bromophenyl)-N-(3-pyridinylmethyl)amine C12H11BrN2 详情 详情
(VI) 13052 4-((5R,5aR,8aR,9S)-9-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxyphenyl dibenzyl phosphate C43H45O16P 详情 详情
(VII) 65016 2,2,2-trifluoro-1-ethanesulfonyl chloride C2H2ClF3O2S 详情 详情

合成路线17

该中间体在本合成路线中的序号：(V)

Coupling of 2-methoxyphenol (I) with 3-fluoronitrobenzene (II) produced the diaryl ether (III). The nitro group of (III) was then reduced by catalytic hydrogenation over Raney-Ni, yielding aniline (IV). Reductive alkylation of (IV) with pyridine-3-carboxaldehyde (V) using NaBH4 furnished the secondary amine (VI). This was finally acylated with 2,2,2-trifluoroethylsulfonyl chloride to produce the title sufonamide.

参考文献 中间体
合成目标
【1】 Monn, J.A.; Hornback, W.J.; Schoepp, D.D.; Dressman, B.A.; Britton, T.C.; Tizzano, J.P.; Johnson, K.W.; Henry, S.S.; Coleman, D.S.; Jagdmann, G.E.J.; Johnson, M.P.; Large, T.H.; Barda, D.A.; Fichtner, M.W. (Eli Lilly and Company); Potentiators of glutamate receptors. WO 0156990 .
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) 13182 Guaiacol; 2-Methoxyphenol 90-05-1 C7H8O2 详情 详情
(II) 55157 1-Fluoro-3-nitrobenzene; 3-Fluoro-1-nitrobenzene; 3-Fluoronitrobenzene; 3-Nitrofluorobenzene; m-Fluoronitrobenzene 402-67-5 C6H4FNO2 详情 详情
(III) 55158 2-methoxyphenyl 3-nitrophenyl ether; 1-methoxy-2-(3-nitrophenoxy)benzene C13H11NO4 详情 详情
(IV) 55159 3-(2-methoxyphenoxy)phenylamine; 3-(2-methoxyphenoxy)aniline C13H13NO2 详情 详情
(V) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(VI) 55160 3-(2-methoxyphenoxy)-N-(3-pyridinylmethyl)aniline; N-[3-(2-methoxyphenoxy)phenyl]-N-(3-pyridinylmethyl)amine C19H18N2O2 详情 详情

合成路线18

该中间体在本合成路线中的序号：(III)

Nitrosation of the benzocycloheptanone (I) with isoamyl nitrite furnishes the keto oxime (II). Subsequent ring closure of (II) with pyridine-3-carboxaldehyde (III) and ammonium acetate produces the N-hydroxy imidazole derivative (IV). Then, reduction of the N-hydroxy group of (IV) is performed by treatment PCl3 in DMF

参考文献 中间体
合成目标
【1】 Satoh, Y.; Hatori, C.; Ito, H.; Novel potent antagonists of human neuropeptide Y-Y5 receptor. Part 4: Tetrahydrodiazabenzazulene derivatives. Bioorg Med Chem Lett 2002, 12, 7, 1009.
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) 60801 3-methyl-5,7,8,9-tetrahydro-6H-benzo[a]cyclohepten-6-one C12H14O 详情 详情
(II) 60802 3-methyl-8,9-dihydro-5H-benzo[a]cycloheptene-5,6(7H)-dione 5-oxime C12H13NO2 详情 详情
(III) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(IV) 60803 9-methyl-2-(3-pyridinyl)-5,6-dihydrobenzo[3,4]cyclohepta[1,2-d]imidazol-1(4H)-ol C18H17N3O 详情 详情

合成路线19

该中间体在本合成路线中的序号：(I)

The reaction of pyridine-3-carbaldehyde (I) with KCN in HOAc/water gives the cyanohydrine (II), which is treated with NH4Cl and NH3 in water to yield 2-amino-2-(3-pyridyl)acetonitrile (III). The cyclization of (III) with S2Cl2 in DMF affords 3-chloro-4-(3-pyridyl)-1,2,5-thiadiazole (IV), which is condensed with tetraethyleneglycol (V) by means of NaH in THF to provide the disubstituted tetraethyleneglycol (VI). The methylation of the pyridine rings of (VI) with methyl iodide in acetone gives the bis N-methylpyridinium derivative (VII), which is finally selectively reduced with NaBH4 in methanol and treated with HCl in the same solvent to furnish the target bis-tetrahydropyridine compound, isolated as the dihydrochloride salt.

参考文献 中间体
合成目标
【1】 Rajeswaran, W.G.; Cao, Y.; Huang, X.-P.; et al.; Design, synthesis, and biological characterization of bivalent 1-methyl-1,2,5,6-tetrahydropyridyl-1,2,5-thiadiazole derivatives as selective muscarinic agonists. J Med Chem 2001, 44, 26, 4563.
【2】 Cao, Y.; Rajeswaran, W.G.; Messer, W.S. (University of Toledo); Muscarinic receptor agonists. US 6211204 .
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) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(II) 53579 2-hydroxy-2-(3-pyridinyl)acetonitrile n/a C7H6N2O 详情 详情
(III) 16175 2-amino-2-(3-pyridinyl)acetonitrile C7H7N3 详情 详情
(IV) 16176 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine C7H4ClN3S 详情 详情
(V) 53580 Tetraethylene glycol; Tetraglycol 112-60-7 C8H18O5 详情 详情
(VI) 53581 3-[4-(2-{2-[2-(2-{[4-(3-pyridinyl)-1,2,5-thiadiazol-3-yl]oxy}ethoxy)ethoxy]ethoxy}ethoxy)-1,2,5-thiadiazol-3-yl]pyridine; 4-(3-pyridinyl)-1,2,5-thiadiazol-3-yl 2-{2-[2-(2-{[4-(3-pyridinyl)-1,2,5-thiadiazol-3-yl]oxy}ethoxy)ethoxy]ethoxy}ethyl ether n/a C22H24N6O5S2 详情 详情
(VII) 53582 1-methyl-3-[4-(2-{2-[2-(2-{[4-(1-methyl-3-pyridiniumyl)-1,2,5-thiadiazol-3-yl]oxy}ethoxy)ethoxy]ethoxy}ethoxy)-1,2,5-thiadiazol-3-yl]pyridinium diiodide n/a C24H30I2N6O5S2 详情 详情

合成路线20

该中间体在本合成路线中的序号：(II)

Metalation of 7-iodoimidazo[5,1-b]thiazole (I) with ethylmagnesium bromide, followed by addition to 3-pyridinecarboxaldehyde (II) provides carbinol (III), which is further oxidized to ketone (IV) by means of MnO2. Lithiation of (IV) and further treatment with chlorotributyltin affords the stannyl derivative (V). The carbapenem ketone (VI) is converted into the vinyl triflate (VII) upon treatment with trifluoromethanesulfonic anhydride and diisopropyl ethylamine. Then, Stille coupling between vinyl triflate (VII) and the stannyl derivative (V) gives rise to the imidazothiazolyl carbapenem (VIII). Quaternization of the pyridine ring of (VIII) with iodoacetamide furnishes the pyridinium salt (IX). Finally the p-nitrobenzyl ester group of (IX) is removed by hydrogenolysis over Pd/C to provide the title compound

参考文献 中间体
合成目标
【1】 Shitara, E.; Yamamoto, Y.; Kano, Y.; Maruyama, T.; Takahashi, M.; Atsumi, K.; CP5609, a novel parenteral carbapenem: Synthesis and structure-activity relationships. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-319.
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) 47193 7-iodoimidazo[5,1-b][1,3]thiazole C5H3IN2S 详情 详情
(II) 12849 Nicotinaldehyde; 3-Pyridinecarboxaldehyde 500-22-1 C6H5NO 详情 详情
(III) 62675 imidazo[5,1-b][1,3]thiazol-7-yl(3-pyridinyl)methanol C11H9N3OS 详情 详情
(IV) 62676 imidazo[5,1-b][1,3]thiazol-7-yl(3-pyridinyl)methanone C11H7N3OS 详情 详情
(V) 62677 3-pyridinyl[2-(tributylstannyl)imidazo[5,1-b][1,3]thiazol-7-yl]methanone C23H33N3OSSn 详情 详情
(VI) 22575 4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate C17H18N2O7 详情 详情
(VII) 38750 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(trifluoromethyl)sulfonyl]oxy]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C18H17F3N2O9S 详情 详情
(VIII) 62678 4-nitrobenzyl (4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[7-(3-pyridinylcarbonyl)imidazo[5,1-b][1,3]thiazol-2-yl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C28H23N5O7S 详情 详情
(IX) 62679 1-(2-amino-2-oxoethyl)-3-{[2-((4S,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-2-{[(4-nitrobenzyl)oxy]carbonyl}-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl)imidazo[5,1-b][1,3]thiazol-7-yl]carbonyl}pyridinium iodide C30H27IN6O8S 详情 详情
Extended Information