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【结 构 式】

【分子编号】54740

【品名】ethyl 4-{[(3R)-1-(2-{(2R)-2-[2-(6-cyano-1-ethyl-1H-indol-2-yl)ethyl]pyrrolidinyl}-2-oxoethyl)-2-oxoazepanyl]amino}butanoate

【CA登记号】

【 分 子 式 】C31H43N5O4

【 分 子 量 】549.71372

【元素组成】C 67.73% H 7.88% N 12.74% O 11.64%

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:(VIII)

The reaction of perhydroazepinone (I) with ethyl 2-bromoacetate (II) by means of LiHMDS in THF, followed by hydrolysis with KOH in methanol/water, gives the perhydroazepinylacetic acid (III), which is condensed with the pyrrolidine derivative (IV) by means of HOBt, WSCl and DIEA in dichloromethane to yield the adduct (V). The cleavage of the carbamate group of (V) with TFA in dichloromethane affords the 3-aminoperhydroazepinone (VI), which is condensed with ethyl 4-bromobutyrate (VII) by means of DIEA in acetonitrile to provide the 4-aminobutyrate derivative (VIII). The reaction of the cyano group of (VIII) with HCl in ethanol, followed by amonolysis with NH3 in the same solvent, gives the carboxamidine derivative (IX), which is hydrolyzed with KOH in ethanol/water to yield the target butyric acid derivative.

1 Park, C.-H.; Koo, B.-A.; Nam, W.-H. (C & C Research Laboratories); Substd. aromatic amidine deriv. and medicinal compsn. comprising the same. WO 0055156 .
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) 54736 2,2-dimethyl-N-[(3R)-2-oxoazepanyl]propanamide C11H20N2O2 详情 详情
(II) 16640 Ethyl 2-bromoacetate; Ethyl bromoacetate 105-36-2 C4H7BrO2 详情 详情
(III) 54737 2-{(3R)-3-[(2,2-dimethylpropanoyl)amino]-2-oxoazepanyl}acetic acid C13H22N2O4 详情 详情
(IV) 50438 1-ethyl-2-[2-[(2S)pyrrolidinyl]ethyl]-1H-indole-6-carbonitrile C17H21N3 详情 详情
(V) 54738 N-[(3R)-1-(2-{(2R)-2-[2-(6-cyano-1-ethyl-1H-indol-2-yl)ethyl]pyrrolidinyl}-2-oxoethyl)-2-oxoazepanyl]-2,2-dimethylpropanamide C30H41N5O3 详情 详情
(VI) 54739 2-[2-((2R)-1-{2-[(3R)-3-amino-2-oxoazepanyl]acetyl}pyrrolidinyl)ethyl]-1-ethyl-1H-indole-6-carbonitrile C25H33N5O2 详情 详情
(VII) 11263 ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate 2969-81-5 C6H11BrO2 详情 详情
(VIII) 54740 ethyl 4-{[(3R)-1-(2-{(2R)-2-[2-(6-cyano-1-ethyl-1H-indol-2-yl)ethyl]pyrrolidinyl}-2-oxoethyl)-2-oxoazepanyl]amino}butanoate C31H43N5O4 详情 详情
(IX) 54741 ethyl 4-[((3R)-1-{2-[(2R)-2-(2-{6-[amino(imino)methyl]-1-ethyl-1H-indol-2-yl}ethyl)pyrrolidinyl]-2-oxoethyl}-2-oxoazepanyl)amino]butanoate C31H46N6O4 详情 详情
Extended Information