|
【结 构 式】 
|
【分子编号】17802 【品名】(6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine 【CA登记号】 |
【 分 子 式 】C8H19N3 【 分 子 量 】157.25908 【元素组成】C 61.1% H 12.18% N 26.72% |
合成路线1
该中间体在本合成路线中的序号：(XV)The reductocondensation of ethanolamine (I) with 3-methylbenzaldehyde (II) by means of NaBH4 gives N-(3-methylbenzyl)ethanolamine (III), which is treated with SOCl2 to yield the 2-chloroethyl derivative (IV). The reaction of (IV) with methylamine (V) affords N-methyl-N'-(3-methylbenzyl)ethane-1,2-diamine (VI), which is condensed with the pyrazole-carboxamide derivative (VII) to provide the unstable compound (VIII)?? (IX). The reduction of (IX) with NaBH4 gives the racemic amide (X), which is submitted to optical resolution by preferential crystallization to yield the (R)-isomer (XI) (1,2). The hydrogenation of (XI) with H2 over Pd/C in ethanol affords the debenzylated compound (XII), which is alkylated by reductocondensation with acetaldehyde (XIII) and NaBH4 in methanol to provide the chiral N-(1-ethyl-4'-methylperhydro-1,4-diazepin-6-(R)-yl)-1H-pyrazole-3-carboxamide (XIV). Finally, this compound is treated with refluxing aqueous HCl to give the corresponding 6(R)-amino derivative (XV).
| 【2】 Hirokawa, Y.; et al.; Synthesis and structure-activity relationships of 4-amino-5-chloro-N-(1,4-dialkylhexahydro-1,4-diazepin-6-yl)-2-methoxybenzamide derivatives, novel and potent serotonin 5-HT3 and dopamine D2 receptors dual antagonist. Chem Pharm Bull 2002, 50, 7, 941. |
| 【1】 Harada, H.; et al.; Synthesis and resolution of (±)-N-[1-methyl-4-(3-methylbenzyl)hexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide by preferential crystallization. Tetrahedron Asymmetry 1997, 8, 14, 2367. |
| 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) | 10259 | Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol | 141-43-5 | C2H7NO | 详情 | 详情 |
| (II) | 41077 | 3-methylbenzaldehyde | 620-23-5 | C8H8O | 详情 | 详情 |
| (III) | 58175 | 2-[(3-methylbenzyl)amino]-1-ethanol | C10H15NO | 详情 | 详情 | |
| (IV) | 58176 | 2-chloro-N-(3-methylbenzyl)-1-ethanamine; N-(2-chloroethyl)-N-(3-methylbenzyl)amine | C10H14ClN | 详情 | 详情 | |
| (V) | 11021 | Methanamine; Methylamine | 74-89-5 | CH5N | 详情 | 详情 |
| (VI) | 54009 | N~1~-methyl-N~2~-(3-methylbenzyl)-1,2-ethanediamine; N-methyl-N-{2-[(3-methylbenzyl)amino]ethyl}amine | n/a | C11H18N2 | 详情 | 详情 |
| (VII) | 58177 | ethyl 3-{[(1-formylvinyl)amino]carbonyl}-1H-indazole-1-carboxylate | C14H13N3O4 | 详情 | 详情 | |
| (VIII) | 58178 | ethyl 3-({[1-formyl-2-(methyl{2-[(3-methylbenzyl)amino]ethyl}amino)ethyl]amino}carbonyl)-1H-indazole-1-carboxylate | C25H31N5O4 | 详情 | 详情 | |
| (IX) | 58179 | 6-({[1-(ethoxycarbonyl)-1H-indazol-3-yl]carbonyl}amino)-4-methyl-1-(3-methylbenzyl)-3,4,5,6-tetrahydro-2H-1,4-diazepin-1-ium | C25H30N5O3 | 详情 | 详情 | |
| (X) | 58180 | N-[1-methyl-4-(3-methylbenzyl)-1,4-diazepan-6-yl]-1H-indazole-3-carboxamide | C22H27N5O | 详情 | 详情 | |
| (XI) | 58181 | N-[(6S)-1-methyl-4-(3-methylbenzyl)-1,4-diazepan-6-yl]-1H-indazole-3-carboxamide | C22H27N5O | 详情 | 详情 | |
| (XII) | 58182 | N-[(6S)-1-methyl-1,4-diazepan-6-yl]-1H-indazole-3-carboxamide | C14H19N5O | 详情 | 详情 | |
| (XIII) | 11974 | Acetaldehyde | 75-07-0 | C2H4O | 详情 | 详情 |
| (XIV) | 58183 | N-[(6S)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-1H-indazole-3-carboxamide | C16H23N5O | 详情 | 详情 | |
| (XV) | 17802 | (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine | C8H19N3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XV)The methylation of 2-hydroxy-4-(4-methylphenylsulfonamido)benzoic acid (XVI) with dimethyl sulfate and KOH in refluxing acetone gives the N,O-dimethylated benzoic acid (XVII), which is chlorinated by means of NCS in hot DMF to yield the chlorobenzoic acid derivative (XVIII). The hydrolysis of (XVIII) with H2SO4 affords 5-chloro-3-methoxy-4-(methylamino)benzoic acid (XIX), which is finally condensed with the aminodiazepine (XV) by means of EDC in dichloromethane to obtain the target chiral benzamide derivative.
| 【1】 Hirokawa, Y.; et al.; Synthesis and structure-activity relationships of 4-amino-5-chloro-N-(1,4-dialkylhexahydro-1,4-diazepin-6-yl)-2-methoxybenzamide derivatives, novel and potent serotonin 5-HT3 and dopamine D2 receptors dual antagonist. Chem Pharm Bull 2002, 50, 7, 941. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XV) | 17802 | (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine | C8H19N3 | 详情 | 详情 | |
| (XVI) | 58184 | 2-hydroxy-4-{[(4-methylphenyl)sulfonyl]amino}benzoic acid | C14H13NO5S | 详情 | 详情 | |
| (XVII) | 58185 | 2-methoxy-4-{methyl[(4-methylphenyl)sulfonyl]amino}benzoic acid | C16H17NO5S | 详情 | 详情 | |
| (XVIII) | 58186 | 5-chloro-2-methoxy-4-{methyl[(4-methylphenyl)sulfonyl]amino}benzoic acid | C16H16ClNO5S | 详情 | 详情 | |
| (XIX) | 31708 | 2-Methoxy-4-methylamino-5-chlorobenzoic acid; 5-Chloro-2-methoxy-4-(methylamino)benzoic acid | C9H10ClNO3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(VIII)Esterification of 2,6-difluoronicotinic acid (I) with methanol and sulfuric acid afforded methyl ester (II). This was treated with methylamine in DMF at 5 C to give a 2:1 mixture of the desired 6-methylaminonicotinate (III) and its regioisomer (IV), which were separated by column chromatography. Reaction of (III) with potassium methoxide generated from methanol and potassium tert-butoxide yielded methyl ether (V). Then, bromination with N-bromosuccinimide in DMF gave bromoester (VI), which was subsequently hydrolyzed with aqueous NaOH to provide acid (VII). Finally, the target amide was prepared by condensation of acid (VII) with the chiral amine (VIII) in the presence of carbonyldiimidazole.
| 【1】 Hirokawa, Y.; Yoshida, N.; Kato, S.; Synthesis of N-(1-ethyl-4-methylhexahydro-1,4-diazepin-6-yl)nicotinamides and their affinities for 5-HT3 and dopamine D2 receptors. Bioorg Med Chem Lett 1998, 8, 12, 1551. |
| 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) | 17795 | 2,6-difluoronicotinic acid | C6H3F2NO2 | 详情 | 详情 | |
| (II) | 17796 | methyl 2,6-difluoronicotinate | C7H5F2NO2 | 详情 | 详情 | |
| (III) | 17797 | methyl 2-fluoro-6-(methylamino)nicotinate | C8H9FN2O2 | 详情 | 详情 | |
| (IV) | 17798 | methyl 6-fluoro-2-(methylamino)nicotinate | C8H9FN2O2 | 详情 | 详情 | |
| (V) | 17799 | methyl 2-methoxy-6-(methylamino)nicotinate | C9H12N2O3 | 详情 | 详情 | |
| (VI) | 17800 | methyl 5-bromo-2-methoxy-6-(methylamino)nicotinate | C9H11BrN2O3 | 详情 | 详情 | |
| (VII) | 17801 | 5-bromo-2-methoxy-6-(methylamino)nicotinic acid | C8H9BrN2O3 | 详情 | 详情 | |
| (VIII) | 17802 | (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine | C8H19N3 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(X)The protection of the NH2 group of L-serine (I) gives N-(benzyloxycarbonyl)-L-serine (II), which is converted into the N-methylamide (III). The reduction of the amide group of (III) affords the diaminopropanol (IV), which is N-protected to provide the Boc-protected compound (V). The mesylation of the OH group of (V) gives the mesylate (VI), which is treated with ethylamine to yield the triaminopropane (VII). Boc deprotection in (VII) with HCl affords intermediate (VIII), which is submitted to a reductive cyclization with glyoxal and BH3/TEA to provide the perhydro-1,4-diazepine (IX). Cbz deprotection in (IX) by hydrogenation with H2 over Pd/C gives the 1-ethyl-4-methylperhydro-1,4-diazepin-6(R)-amine (X), which is condensed with 5-bromo-2-methoxy-6-(methylamino)pyridine-3-carboxylic acid (XI) by means of ethyl chloroformate and TEA to yield the target amide (XII). Finally, this compound is treated with fumaric acid (XIII) in ethanol to afford the desired fumarate salt.
| 【1】 Hirokawa, Y.; et al.; Process development of the synthetic route to (R)-6-amino-1-ethyl-4-methylhexahydro-1,4-diazepine. Org Process Res Dev 2002, 6, 1, 28. |
| 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) | 20915 | methyl (2S)-2-amino-3-hydroxypropanoate | 5680-80-8 | C4H9NO3 | 详情 | 详情 |
| (II) | 51660 | methyl (2S)-2-[[(benzyloxy)carbonyl]amino]-3-hydroxypropanoate | C12H15NO5 | 详情 | 详情 | |
| (III) | 53991 | benzyl (1S)-1-(hydroxymethyl)-2-(methylamino)-2-oxoethylcarbamate | n/a | C12H16N2O4 | 详情 | 详情 |
| (IV) | 53992 | benzyl (1R)-2-hydroxy-1-[(methylamino)methyl]ethylcarbamate | n/a | C12H18N2O3 | 详情 | 详情 |
| (V) | 53993 | benzyl (1R)-2-[(tert-butoxycarbonyl)(methyl)amino]-1-(hydroxymethyl)ethylcarbamate | n/a | C17H26N2O5 | 详情 | 详情 |
| (VI) | 53994 | (2R)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)(methyl)amino]propyl methanesulfonate | n/a | C18H28N2O7S | 详情 | 详情 |
| (VII) | 53995 | benzyl (1S)-2-[(tert-butoxycarbonyl)(methyl)amino]-1-[(ethylamino)methyl]ethylcarbamate | n/a | C19H31N3O4 | 详情 | 详情 |
| (VIII) | 53996 | benzyl (1R)-2-(ethylamino)-1-[(methylamino)methyl]ethylcarbamate | n/a | C14H23N3O2 | 详情 | 详情 |
| (IX) | 53997 | benzyl (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylcarbamate | n/a | C16H25N3O2 | 详情 | 详情 |
| (X) | 17802 | (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine | C8H19N3 | 详情 | 详情 | |
| (XI) | 17801 | 5-bromo-2-methoxy-6-(methylamino)nicotinic acid | C8H9BrN2O3 | 详情 | 详情 | |
| (XII) | 53998 | 5-bromo-N-[(6S)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-2-methoxy-6-(methylamino)nicotinamide | n/a | C16H26BrN5O2 | 详情 | 详情 |
| (XIII) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(XIII)The protection of the NH2 group of L-serine (I) gives N-(benzyloxycarbonyl)-L-serine (II), which is converted into the N-methylamide (III). The reduction of the amide group of (III) affords the diaminopropanol (IV), which is N-protected to provide the Boc-protected compound (V). The mesylation of the OH group of (V) gives the mesylate (VI), which is treated with ethylamine to yield the triaminopropane (VII). The condensation of (VII) with ethyl bromoacetate (VIII) affords the aminoacetate (IX), which is selectively deprotected with HCl to provide the intermediate (X). The cyclization of (X) by means of NaOEt gives the perhydro-1,4-diazepin-2-one (XI), which is reduced with BH3/THF to yield the perhydro-1,4-diazepine (XII). Cbz deprotection in (XII) by hydrogenation with H2 over Pd/C gives the 1-ethyl-4-methylperhydro-1,4-diazepin-6(R)-amine (XIII), which is condensed with 5-bromo-2-methoxy-6-(methylamino)pyridine-3-carboxylic acid (XIV) by means of ethyl chloroformate and TEA to yield the target amide (XV). Finally, this compound is treated with fumaric acid (XVI) in ethanol to afford the desired fumarate salt.
| 【1】 Hirokawa, Y.; et al.; Process development of the synthetic route to (R)-6-amino-1-ethyl-4-methylhexahydro-1,4-diazepine. Org Process Res Dev 2002, 6, 1, 28. |
| 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) | 20915 | methyl (2S)-2-amino-3-hydroxypropanoate | 5680-80-8 | C4H9NO3 | 详情 | 详情 |
| (II) | 51660 | methyl (2S)-2-[[(benzyloxy)carbonyl]amino]-3-hydroxypropanoate | C12H15NO5 | 详情 | 详情 | |
| (III) | 53991 | benzyl (1S)-1-(hydroxymethyl)-2-(methylamino)-2-oxoethylcarbamate | n/a | C12H16N2O4 | 详情 | 详情 |
| (IV) | 53992 | benzyl (1R)-2-hydroxy-1-[(methylamino)methyl]ethylcarbamate | n/a | C12H18N2O3 | 详情 | 详情 |
| (V) | 53993 | benzyl (1R)-2-[(tert-butoxycarbonyl)(methyl)amino]-1-(hydroxymethyl)ethylcarbamate | n/a | C17H26N2O5 | 详情 | 详情 |
| (VI) | 53994 | (2R)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)(methyl)amino]propyl methanesulfonate | n/a | C18H28N2O7S | 详情 | 详情 |
| (VII) | 53995 | benzyl (1S)-2-[(tert-butoxycarbonyl)(methyl)amino]-1-[(ethylamino)methyl]ethylcarbamate | n/a | C19H31N3O4 | 详情 | 详情 |
| (VIII) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (IX) | 53999 | ethyl 2-[{(2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)(methyl)amino]propyl}(ethyl)amino]acetate | n/a | C23H37N3O6 | 详情 | 详情 |
| (X) | 54000 | ethyl 2-[[(2R)-2-{[(benzyloxy)carbonyl]amino}-3-(methylamino)propyl](ethyl)amino]acetate | n/a | C18H29N3O4 | 详情 | 详情 |
| (XI) | 54001 | benzyl (6S)-4-ethyl-1-methyl-2-oxo-1,4-diazepan-6-ylcarbamate | n/a | C16H23N3O3 | 详情 | 详情 |
| (XII) | 53997 | benzyl (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylcarbamate | n/a | C16H25N3O2 | 详情 | 详情 |
| (XIII) | 17802 | (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine | C8H19N3 | 详情 | 详情 | |
| (XIV) | 17801 | 5-bromo-2-methoxy-6-(methylamino)nicotinic acid | C8H9BrN2O3 | 详情 | 详情 | |
| (XV) | 53998 | 5-bromo-N-[(6S)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-2-methoxy-6-(methylamino)nicotinamide | n/a | C16H26BrN5O2 | 详情 | 详情 |
| (XVI) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(IX)The protection of the NH2 group of L-serine (I) with Ts-Cl and TEA gives N-tosyl-L-serine (II), which is converted into the N-methylamide (III). The cyclization of (III) by means of diisopropylazodicarboxylate (DIAD) yields the N-tosylaziridine (IV), which is treated with ethylamine (V) to afford the diaminopropionamide (VI). The reduction of the amide group of (VI) with LiAlH4 provides the triaminopropane (VII), which is submitted to a reductive cyclization with glyoxal and BH3/TEA to give the perhydro-1,4-diazepine (VIII). Ts deprotection in (VIII) by means of HBr affords the 1-ethyl-4-methylperhydro-1,4-diazepin-6(R)-amine (IX), which is condensed with 5-bromo-2-methoxy-6-(methylamino)pyridine-3-carboxylic acid (X) by means of ethyl chloroformate and TEA to yield the target amide (XI). Finally, this compound is treated with fumaric acid (XII) in ethanol to afford the desired fumarate salt.
| 【1】 Hirokawa, Y.; et al.; Process development of the synthetic route to (R)-6-amino-1-ethyl-4-methylhexahydro-1,4-diazepine. Org Process Res Dev 2002, 6, 1, 28. |
| 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) | 20915 | methyl (2S)-2-amino-3-hydroxypropanoate | 5680-80-8 | C4H9NO3 | 详情 | 详情 |
| (II) | 54002 | methyl (2S)-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}propanoate | n/a | C11H15NO5S | 详情 | 详情 |
| (III) | 54003 | (2S)-3-hydroxy-N-methyl-2-{[(4-methylphenyl)sulfonyl]amino}propanamide | n/a | C11H16N2O4S | 详情 | 详情 |
| (IV) | 54004 | (2S)-N-methyl-1-[(4-methylphenyl)sulfonyl]-2-aziridinecarboxamide | n/a | C11H14N2O3S | 详情 | 详情 |
| (V) | 10928 | Ethanamine | 75-04-7 | C2H7N | 详情 | 详情 |
| (VI) | 54005 | (2S)-3-(ethylamino)-N-methyl-2-{[(4-methylphenyl)sulfonyl]amino}propanamide | n/a | C13H21N3O3S | 详情 | 详情 |
| (VII) | 54006 | N-{(1R)-2-(ethylamino)-1-[(methylamino)methyl]ethyl}-4-methylbenzenesulfonamide | n/a | C13H23N3O2S | 详情 | 详情 |
| (VIII) | 54007 | N-[(6S)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-4-methylbenzenesulfonamide | n/a | C15H25N3O2S | 详情 | 详情 |
| (IX) | 17802 | (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine | C8H19N3 | 详情 | 详情 | |
| (X) | 17801 | 5-bromo-2-methoxy-6-(methylamino)nicotinic acid | C8H9BrN2O3 | 详情 | 详情 | |
| (XI) | 53998 | 5-bromo-N-[(6S)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-2-methoxy-6-(methylamino)nicotinamide | n/a | C16H26BrN5O2 | 详情 | 详情 |
| (XII) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(XVIII)The reaction of N-methyl-N'-(3-methylbenzyl)ethylene-1,2-diamine (VIII) with (Boc)2O in chloroform gives N-(tert-butoxycarbonyl)-N-methyl-N'-(3-methylbenzyl)ethylene-1,2-diamine (IX), which is condensed with the chiral aziridine (X) by heating at 80 C to yield the diaminobutyric ester (XI). Selective elimination of the Boc protecting group of (XI) with HCl in methanol affords the methylamino intermediate (XII), which is treated with NaOH in ethanol/water to provide the carboxylic acid (XIII). The cyclization of (XIII) by means of DEC gives the perhydro-1,4-diazepin-5-one derivative (XIV), which is debenzylated by means of 1-chloroethyl chloroformate to yield the 6(S)-(benzyloxycarbonylamino)-4-methylperhydro-1,4-diazepin-5-one (XV). The reductive alkylation of (XV) with acetaldehyde, NaBH4 and TEA in methanol affords the 1-ethyl derivative (XVI), which is deprotected by means of conc. HBr to provide 6(S)-amino-1-ethyl-4-methylperhydro-1,4-diazepin-5-one (XVII). The reduction of (XVII) with BH3/THF gives 1-ethyl-4-methylperhydro-1,4-diazepin-6(R)-amine (XVIII), which is condensed with 5-bromo-2-methoxy-6-(methylamino)pyridine-3-carboxylic acid (VII) by means of ethyl chloroformate and TEA to yield the target amide (XIX). Finally, this compound is treated with fumaric acid (XX) in ethanol to afford the desired fumarate salt.
| 【1】 Kato, S.; Hirokawa, Y.; Morie, T.; Harada, H.; Yoshida, N. (Dainippon Pharmaceutical Co., Ltd.); (R)-5-Bromo-N-(1-ethyl-4-methylhexahydro-1H-1, 4-diazepin-6-yl)-2-methoxy-6-methylamino-3-pyridine-carboxamide, process for producing the same and medicinal compsn. containing the same. EP 0855397; JP 1997100276; JP 1997118669; US 5945415; WO 9705129 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VII) | 17801 | 5-bromo-2-methoxy-6-(methylamino)nicotinic acid | C8H9BrN2O3 | 详情 | 详情 | |
| (VIII) | 54009 | N~1~-methyl-N~2~-(3-methylbenzyl)-1,2-ethanediamine; N-methyl-N-{2-[(3-methylbenzyl)amino]ethyl}amine | n/a | C11H18N2 | 详情 | 详情 |
| (IX) | 54010 | tert-butyl methyl{2-[(3-methylbenzyl)amino]ethyl}carbamate | n/a | C16H26N2O2 | 详情 | 详情 |
| (X) | 54011 | 1-benzyl 2-methyl (2S)-1,2-aziridinedicarboxylate | n/a | C12H13NO4 | 详情 | 详情 |
| (XI) | 54012 | methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-[{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}(3-methylbenzyl)amino]butanoate | n/a | C29H41N3O6 | 详情 | 详情 |
| (XII) | 54013 | methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-[[2-(methylamino)ethyl](3-methylbenzyl)amino]butanoate | n/a | C24H33N3O4 | 详情 | 详情 |
| (XIII) | 54014 | (2S)-2-{[(benzyloxy)carbonyl]amino}-4-[[2-(methylamino)ethyl](3-methylbenzyl)amino]butanoic acid | n/a | C23H31N3O4 | 详情 | 详情 |
| (XIV) | 54015 | benzyl (6S)-4-methyl-1-(3-methylbenzyl)-5-oxo-1,4-diazepan-6-ylcarbamate | n/a | C22H27N3O3 | 详情 | 详情 |
| (XV) | 54016 | benzyl (6S)-1-methyl-7-oxo-1,4-diazepan-6-ylcarbamate | n/a | C14H19N3O3 | 详情 | 详情 |
| (XVI) | 54017 | benzyl (6S)-1-ethyl-4-methyl-5-oxo-1,4-diazepan-6-ylcarbamate | n/a | C16H23N3O3 | 详情 | 详情 |
| (XVII) | 54018 | (6S)-6-amino-1-ethyl-4-methyl-1,4-diazepan-5-one | n/a | C8H17N3O | 详情 | 详情 |
| (XVIII) | 17802 | (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine | C8H19N3 | 详情 | 详情 | |
| (XIX) | 53998 | 5-bromo-N-[(6S)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-2-methoxy-6-(methylamino)nicotinamide | n/a | C16H26BrN5O2 | 详情 | 详情 |
| (XX) | 23808 | Fumaric acid; (E)-2-butenedioic acid | 110-17-8 | C4H4O4 | 详情 | 详情 |