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【结 构 式】

【分子编号】14054

【品名】8-Acetyl-5-(2-chlorophenyl)-3-methyl-1,3,6,7,8,9-hexahydro-2H-pyrido[4',3':4,5]thieno[2,3-e][1,4]diazepin-2-one

【CA登记号】

【 分 子 式 】C19H18ClN3O2S

【 分 子 量 】387.88964

【元素组成】C 58.83% H 4.68% Cl 9.14% N 10.83% O 8.25% S 8.27%

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:(V)

1-Acetyl-4-piperidone (I) is condensed with 2-chlorocyanoacetophenone in the presence of sulfur and base to give the thiophene (II). Treatment of (II) with 2-bromopropionyl bromide gives the amide (III), which on reaction with ammonia gives the amine (IV). Cyclization of (IV) with acetic acid/pyridine gives the diazepine (V). Reaction of the amide of (V) with phosphorus pentasulfide or Lawesson's reagent produces the thioamide (VI), which is reacted with acetic hydrazide to give the triazole (VII). Basic hydrolysis of the amide of (VII) produces the amine (VIII), which is resolved to give the S-enantiomer (IX). Reaction of (IX) with cyclopropanecarbonyl chloride gives the amide (X).

1 1,4-Diazepine deriv. and its pharmaceutical use. AU 8943761; EP 0367110; EP 0606103; EP 0677524; JP 1990256682; US 5221671; US 5304553; US 5382579; US 5409909; US 5438045; US 5468740; US 5482937 .
2 Clark, R.S.J.; E6123. Drugs Fut 1991, 16, 4, 310.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12923 3-(2-Chlorophenyl)-3-oxopropanenitrile 40018-25-5 C9H6ClNO 详情 详情
14061 Cyclopropanecarbonyl chloride; Cyclopropanecarboxylic acid chloride 4023-34-1 C4H5ClO 详情 详情
(I) 14050 N-Acetyl-4-piperidone; 1-Acetyltetrahydro-4(1H)-pyridinone 32161-06-1 C7H11NO2 详情 详情
(II) 14051 1-[2-Amino-3-(2-chlorobenzoyl)-4,7-dihydrothieno[2,3-c]pyridin-6(5H)-yl]-1-ethanone C16H15ClN2O2S 详情 详情
(III) 14052 N-[6-Acetyl-3-(2-chlorobenzoyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl]-2-bromopropanamide C19H18BrClN2O3S 详情 详情
(IV) 14053 N-[6-Acetyl-3-(2-chlorobenzoyl)-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl]-2-aminopropanamide C19H20ClN3O3S 详情 详情
(V) 14054 8-Acetyl-5-(2-chlorophenyl)-3-methyl-1,3,6,7,8,9-hexahydro-2H-pyrido[4',3':4,5]thieno[2,3-e][1,4]diazepin-2-one C19H18ClN3O2S 详情 详情
(VI) 14055 5-(2-Chlorophenyl)-8-ethanethioyl-3-methyl-1,3,6,7,8,9-hexahydro-2H-pyrido[4',3':4,5]thieno[2,3-e][1,4]diazepine-2-thione C19H18ClN3S3 详情 详情
(VII) 14056 1-[6-(2-Chlorophenyl)-1,4-dimethyl-7,10-dihydro-4H-pyrido[4',3':4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin-9(8H)-yl]-1-ethanethione C21H20ClN5S2 详情 详情
(VIII) 14057 6-(2-Chlorophenyl)-1,4-dimethyl-7,8,9,10-tetrahydro-4H-pyrido[4',3':4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine C19H18ClN5S 详情 详情
(IX) 14058 (4S)-6-(2-Chlorophenyl)-1,4-dimethyl-7,8,9,10-tetrahydro-4H-pyrido[4',3':4,5]thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine C19H18ClN5S 详情 详情
Extended Information