• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】32633

【品名】2-[[5-(2-chlorophenyl)-7-nitro-3H-1,4-benzodiazepin-2-yl]amino]acetic acid

【CA登记号】

【 分 子 式 】C17H13ClN4O4

【 分 子 量 】372.76748

【元素组成】C 54.78% H 3.52% Cl 9.51% N 15.03% O 17.17%

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:(II)

The reaction of 5-(2-chlorophenyl)-7-nitro-3H-1,4-benzodiazepin-2-thione (I) with glycine (A) by means of Na2CO3 in refluxing ethanol-water gives 2-carboxymethylamino-7-nitro-5-(2-chlorophenyl)-3H-1,4-benzodiazepine (II), which is cyclized by means of dicyclohexylcarbodiimide in methylene chloride to afford 8-nitro-(2-chlorophenyl)-1,2-dihydro-1H,4H-imidazo[1,2-a][1,4]benzodiazepin-1-one (III). The reaction of (III) with dimethylformamide diethylacetal (B) by means of triethylamine in benzene yields 8-nitro-2-(dimethylaminomethylene)-6-(2-chlorophenyl)-1,2-dihydro-1H,4H-imidazo[1,2a][1,4]benzodiazepin-1-one (IV), which is treated with N-methylpiperazine (C) in refluxing toluene to produce 8-nitro-(2-chlorophenyl)-2-(N-methylpiperazin-1-ylmethylene)-1,2-dihydro-1H,4H-imidazo [1,2-a][1,4]benzodiazepin-1-one (V). This compound is finally treated with methanesulfonic acid.

1 Taylor, J.B.; Harrison D.R.; 1,2-Dihydro-6-phenyl-1H,4H-imidazobenzodiazepin-1-ones. US 4044142 .
2 Ager, J.R.; et al.; Central nervous system activity of a novel class of annelated 1,4-benzodiazwpines, aminomethylene-2,4-dihydro-1H-imidazo[1,2-a][1,4]benzodiazepin-1-ones. J Med Chem 1977, 20, 8, 1035-41.
3 Thorpe, P.J.; Castaner, J.; Blancafort, P.; Serradell, M.N.; RU-31,158. Drugs Fut 1980, 5, 3, 144.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
40922 N,N'-dicyclohexylurea 2387-23-7 C13H24N2O 详情 详情
(A) 20436 glycine 56-40-6 C2H5NO2 详情 详情
(B) 31457 N-(diethoxymethyl)-N,N-dimethylamine; diethoxy-N,N-dimethylmethanamine 1188-33-6 C7H17NO2 详情 详情
(I) 32632 5-(2-chlorophenyl)-7-nitro-1,3-dihydro-2H-1,4-benzodiazepine-2-thione C15H10ClN3O2S 详情 详情
(II) 32633 2-[[5-(2-chlorophenyl)-7-nitro-3H-1,4-benzodiazepin-2-yl]amino]acetic acid C17H13ClN4O4 详情 详情
(III) 30373 6-(2-chlorophenyl)-8-nitro-2,4-dihydro-1H-imidazo[1,2-a][1,4]benzodiazepin-1-one C17H11ClN4O3 详情 详情
(IV) 32634 6-(2-chlorophenyl)-2-[(Z)-(dimethylamino)methylidene]-8-nitro-1H-imidazo[1,2-a][1,4]benzodiazepin-1(4H)-one C20H16ClN5O3 详情 详情
(V) 30375 6-(2-chlorophenyl)-2-[(Z)-(4-methyl-1-piperazinyl)methylidene]-8-nitro-1H-imidazo[1,2-a][1,4]benzodiazepin-1(4H)-one C23H21ClN6O3 详情 详情
(C) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
Extended Information