methyl 5-amino-1H-indole-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】59131

【品名】methyl 5-amino-1H-indole-2-carboxylate

【CA登记号】

【分子式】C₁₀H₁₀N₂O₂

【分子量】190.20168

【元素组成】C 63.15% H 5.3% N 14.73% O 16.82%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(IX)

Condensation of 5-aminoindole-2-carboxylic acid ethyl ester (IX) with phosgene at very low temperature furnished the N,N'-bis(indolyl)urea (X). Subsequent basic hydrolysis of the ethyl ester groups of (X) gave diacid (XI). This was finally coupled with the intermediate pyrroloindole (VIII) by means of EDC to provide the title diamide.

参考文献中间体

合成目标

【1】 Fukuda, Y.; et al.; Novel syntheses of optically active CC-1065, U-73,975 (adozelesin), U-80,244 (carzelesin), U-77,779 (bizelesin), KW-2189, and DU-86. Heterocycles 1997, 45, 12, 2303.
【2】 Kelly, R.C.; Aristoff, P.A. (Pharmacia Corp.); Novel CC-1065 analogs having two CPI subunits. EP 0359454; JP 1992500664; WO 9002746 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(VIII)	59130	(8S)-8-(chloromethyl)-1-methyl-3,6,7,8-tetrahydropyrrolo[3,2-e]indol-4-ol	C₁₂H₁₃ClN₂O	详情	详情
(IX)	59131	methyl 5-amino-1H-indole-2-carboxylate	C₁₀H₁₀N₂O₂	详情	详情
(X)	59132	methyl 5-[({[2-(methoxycarbonyl)-1H-indol-5-yl]amino}carbonyl)amino]-1H-indole-2-carboxylate	C₂₁H₁₈N₄O₅	详情	详情
(XI)	59133	5-({[(2-carboxy-1H-indol-5-yl)amino]carbonyl}amino)-1H-indole-2-carboxylic acid	C₁₉H₁₄N₄O₅	详情	详情

Extended Information