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

【结 构 式】

【分子编号】61065

【品名】2-bromo-4-(2-chlorophenyl)-9-cyclohexyl-5,6-dihydro-4H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

【CA登记号】

【 分 子 式 】C20H20BrClN4S

【 分 子 量 】463.82846

【元素组成】C 51.79% H 4.35% Br 17.23% Cl 7.64% N 12.08% S 6.91%

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)

The reduction of 2-chloroacetylamino-3-(o-chlorobenzoyl)thiophene (I) with NaBH4 in DMF gives 2-chloroacetylamino-3-[(o-chlorophenyl)hydroxymethyl]thiophene (II), which is cyclized by means of sodium isopropoxide in refluxing isopropanol to afford 5-(o-chlorophenyl)thieno[2,3-e]-4,1-oxazepin-2-one (III). The bromination of (III) with Br2 in CHCl3 - pyridine yields 7-bromo-5-(o-chlorophenyl)thieno[2,3-e]-4,1-oxazepin-2-one (IV), which by reaction with P2S5 and NaHCO3 in hot diglyme is converted into 7-bromo-5-(o-chlorophenyl)thieno[2,3-e]-4,1-oxazepin-2-thione (V) (1). The cyclization of (V) with cyclohexanecarboxyl hydrazide (A) in THF gives 7-bromo-5-(o-chlorophenyl)-1-cyclohexylthieno[2,3-e]triazolo[3,4-c]-4,1-oxazepin-2-one (VI). The ring opening of (VI) by treatment with concentrated HBr yields 3-cyclohexyl-4-[3-(o-chlorophenylbromomethyl)-5-bromo-2-thienyl]-5-hydroxymethyl-1,2,4-triazole (VII), which by reaction with SOCl2 is converted into 3-cyclohexyl-4-[3-(o-chlorophenyl-bromomethyl)-5-bromo-2-thienyl]-5-chloromethyl-1,2,4-triazole (VIII). The cyclization of (VIII) with NH3 in methanol a 100 C in a pressure vessel yields 8-bromo-6-(o-chlorophenyl)-1-cyclohexyl-4H-s-triazolo[3,4-c]thieno[2,3-e]-5,6-dihydro-1,4-diazepine (IX), which is finally dehydrogenated by treatment with KMnO4 in refluxing acetone

1 Weber, K.H.; et al. (C.H. Boehringer Sohn); BE 844170; CA 1077475; DD 126744; DE 2531677; DE 2531678; DE 2531679; DE 2533924; FR 2318165; GB 1550679; GB 1550680; JP 7712189; JP 7712193; JP 7714800; JP 7717496; NL 7607871; NL 7607872; US 4201712; ZA 7604212 .
2 Blancafort, P.; Serradell, M.N.; Castaner, J.; Owen, R.T.; Ciclotizolam. Drugs Fut 1981, 6, 6, 342.
3 Imvamune IND receives approval. Justus Liebigs Ann Chem. 1978, 1257.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 61061 cyclohexanecarbohydrazide C7H14N2O 详情 详情
(I) 61056 2-chloro-N-[3-(2-chlorobenzoyl)-2-thienyl]acetamide C13H9Cl2NO2S 详情 详情
(II) 61057 2-chloro-N-{3-[(2-chlorophenyl)(hydroxy)methyl]-2-thienyl}acetamide C13H11Cl2NO2S 详情 详情
(III) 61058 5-(2-chlorophenyl)-1,5-dihydrothieno[2,3-e][1,4]oxazepin-2(3H)-one C13H10ClNO2S 详情 详情
(IV) 61059 7-bromo-5-(2-chlorophenyl)-1,5-dihydrothieno[2,3-e][1,4]oxazepin-2(3H)-one C13H9BrClNO2S 详情 详情
(V) 60160 (3S,8R,9S,10R,13S,14S,16S,17S)-3-{[tert-butyl(dimethyl)silyl]oxy}-17-[(1S)-1-(2-isopentyl-1,3-dioxolan-2-yl)ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-16,17-diol C35H62O5Si 详情 详情
(VI) 61062 2-bromo-4-(2-chlorophenyl)-9-cyclohexyl-4H,6H-thieno[2,3-e][1,2,4]triazolo[3,4-c][1,4]oxazepine C20H19BrClN3OS 详情 详情
(VII) 60163 4-fluorobenzaldehyde C7H5FO 详情 详情
(VIII) 61064 4-{5-bromo-3-[bromo(2-chlorophenyl)methyl]-2-thienyl}-3-(chloromethyl)-5-cyclohexyl-4H-1,2,4-triazole C20H19Br2Cl2N3S 详情 详情
(IX) 61065 2-bromo-4-(2-chlorophenyl)-9-cyclohexyl-5,6-dihydro-4H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine C20H20BrClN4S 详情 详情
Extended Information