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【结 构 式】

【分子编号】35952

【品名】7-fluoro-2-methyl-5,10-dihydro-4H-thieno[2,3-b][1,5]benzodiazepin-4-one

【CA登记号】

【 分 子 式 】C12H9FN2OS

【 分 子 量 】248.2807432

【元素组成】C 58.05% H 3.65% F 7.65% N 11.28% O 6.44% S 12.92%

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)

The condensation of 2,5-difluoronitrobenzene (I) with ethyl 2-amino-5-methylthiophene-3-carboxylate (II) by means of triethylamine in hot DMSO or 2-methoxyethanol giving ethyl 2-(4-fluoro-2-nitroanilino)-5-methylthiophene-3-carboxylate (III), which is reduced with H2 over Pd/C in ethanol to ethyl 2-(4-fluoro-2-aminoanilino)-5-methylthiophene-3-carboxylate (IV). The cyclization of (IV) by means of NaH in DMSO affords 9,10-dihydro-7-fluoro-2-methyl-4H-thieno[2,3b][1,5]benzodiazepin-2-one (V), which is finally condensed with N-methylpiperazine by means of TiCl4 in anisole at 120 C.

1 Chakrabarti, J.K.; Tupper, D.E.; Benzodiazepine derivatives. DE 2552403; FR 2292479; GB 1533235; JP 51076296 .
2 Pullar, I.A.; Chakrabarti, J.K.; Horsman, L.; Wright, F.C.; Tupper, D.E.; Hotten, T.M.; Heterooarenobenzodiazepines. 3. 4-Piperazinyl-10H-thieno[2,3-b][1,5]benzodiazepines as potential neuroleptics. J Med Chem 1980, 23, 8, 878-884.
3 Blancafort, P.; Castañer, J.; Serradell, M.N.; Flumezapine. Drugs Fut 1983, 8, 2, 110.
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) 32036 2,4-difluoro-1-nitrobenzene 446-35-5 C6H3F2NO2 详情 详情
(II) 35949 ethyl 2-amino-5-methyl-3-thiophenecarboxylate C8H11NO2S 详情 详情
(III) 35950 ethyl 2-(5-fluoro-2-nitroanilino)-5-methyl-3-thiophenecarboxylate C14H13FN2O4S 详情 详情
(IV) 35951 ethyl 2-(2-amino-5-fluoroanilino)-5-methyl-3-thiophenecarboxylate C14H15FN2O2S 详情 详情
(V) 35952 7-fluoro-2-methyl-5,10-dihydro-4H-thieno[2,3-b][1,5]benzodiazepin-4-one C12H9FN2OS 详情 详情
(VI) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
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