Ethyl 5-(2,4-dimethoxybenzyl)-8-fluoro-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate; Ethyl-8-fluoro-5-(2,4dimethoxybenzyl)-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】31968

【品名】Ethyl 5-(2,4-dimethoxybenzyl)-8-fluoro-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate; Ethyl-8-fluoro-5-(2,4dimethoxybenzyl)-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

【CA登记号】

【分子式】C₂₃H₂₂FN₃O₅

【分子量】439.4433032

【元素组成】C 62.86% H 5.05% F 4.32% N 9.56% O 18.2%

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：(X)

The cyclization of anhydride (IV) with N-(2,4-dimethoxybenzyl)glycine (VIII) as before gives 7-fluoro-4-(2,4dimethoxybenzyl)-3,4-dihydro-2H-1,4-benzodiazepin-2,5(1H)-dione (IX), which by a new cyclization with (VII) as before is converted into ethyl-8-fluoro-5-(2,4dimethoxybenzyl)-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate (X). The deprotection of (X) with trifluoroacetic acid yields ethyl-8-fluoro-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate (XI), which is finally methylated with methyl iodide and NaH in DMF.

参考文献中间体

合成目标

【1】 Haefely, W.; Hunkeler, W.; Kyburz, E.; Mohler, H.; Pieri, L.; Polc, P.; Gerecke, M. (F. Hoffmann-La Roche AG); Imidazodiazepine derivatives. EP 0027214; GB 2060632; JP 1156968; US 4316839; US 4346033 .
【2】 Blancafort, P.; Castaner, J.; Hillier, K.; Serradell, M.N.; RO-15-1788. Drugs Fut 1982, 7, 6, 402.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	31964	6-Fluoro-2H-3,1-benzoxazine-2,4(1H)-dione; 5-Fluoroisatoic acid anhydride		C₈H₄FNO₃	详情	详情
(VII)	11877	Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate	105-56-6	C₅H₇NO₂	详情	详情
(VIII)	31966	N-(2,4-dimethoxybenzyl)glycine; 2-[(2,4-Dimethoxybenzyl)amino]acetic acid		C₁₁H₁₅NO₄	详情	详情
(IX)	31967	4-(2,4-dimethoxybenzyl)-7-fluoro-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione		C₁₈H₁₇FN₂O₄	详情	详情
(X)	31968	Ethyl 5-(2,4-dimethoxybenzyl)-8-fluoro-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate; Ethyl-8-fluoro-5-(2,4dimethoxybenzyl)-5,6-dihydro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate		C₂₃H₂₂FN₃O₅	详情	详情
(XI)	31969	ethyl 8-fluoro-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate		C₁₄H₁₂FN₃O₃	详情	详情

Extended Information