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【结 构 式】

【分子编号】25906

【品名】9-methoxy-1-phenyl-6,7-dihydro[1,4]diazepino[6,7,1-hi]indol-4(3H)-one

【CA登记号】

【 分 子 式 】C18H16N2O2

【 分 子 量 】292.33732

【元素组成】C 73.95% H 5.52% N 9.58% O 10.95%

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:(VI)

The hydrogenation of 5-methoxy-1H-indole (I) by means of NaCNBH3 in acetic acid gives 5-methoxyindoline (II), which is benzoylated with benzonitrile (III) by means of BCl3/AlCl3 in dichloroethane yielding 7-benzoyl-5-methoxyindoline (IV). The cyclization of (IV) with glycine ethyl ester (V) in pyridine affords the pyrrolo[1,4]benzodiazepine (VI), which is treated with amyl nitrite in toluene/THF to provide the oxime (VII). The reduction of (VII) with H2 over Ru/C in methanol gives the racemic amine (VIII), which is submitted to optical resolution with di-p-toluoyl-D-tartaric acid yielding the corresponding (R)-isomer (IX). Finally, this compound is condensed with 1H-indole-2-carboxylic acid (X) by means of TOTU and DIEA in dichloromethane.

1 Feru, F.; et al.; Synthesis and structure-activity relationships of 9-methoxy-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-hi]indolines: Novel PDE 4 inhibitors. 216th ACS Natl Meet (Aug. 23-27, Boston) 1998, Abst MEDI 049.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
40665 cyclopentyl nitrite C5H9NO2 详情 详情
(I) 25902 1H-Indol-5-yl methyl ether; 5-Methoxy-1H-indole; 5-Methoxyindole 1006-94-6 C9H9NO 详情 详情
(II) 25903 5-methoxyindoline; 2,3-dihydro-1H-indol-5-yl methyl ether C9H11NO 详情 详情
(III) 25904 benzonitrile 100-47-0 C7H5N 详情 详情
(IV) 25905 (5-methoxy-2,3-dihydro-1H-indol-7-yl)(phenyl)methanone C16H15NO2 详情 详情
(V) 10309 ethyl 2-aminoacetate; Glycine ethyl ester 459-73-4 C4H9NO2 详情 详情
(VI) 25906 9-methoxy-1-phenyl-6,7-dihydro[1,4]diazepino[6,7,1-hi]indol-4(3H)-one C18H16N2O2 详情 详情
(VII) 25907 9-methoxy-1-phenyl-6,7-dihydro[1,4]diazepino[6,7,1-hi]indole-3,4-dione 3-oxime C18H15N3O3 详情 详情
(VIII) 25908 3-amino-9-methoxy-1-phenyl-6,7-dihydro[1,4]diazepino[6,7,1-hi]indol-4(3H)-one C18H17N3O2 详情 详情
(IX) 25909 (3R)-3-amino-9-methoxy-1-phenyl-6,7-dihydro[1,4]diazepino[6,7,1-hi]indol-4(3H)-one C18H17N3O2 详情 详情
(X) 25226 1H-Indole-2-carboxylic acid; Indole-2-carboxylic acid 1477-50-5 C9H7NO2 详情 详情
Extended Information