(3,4-Diaminophenyl)phenylmethanone; 3,4-Diaminobenzophenone -Drug Synthesis Database

【结构式】

【分子编号】12830

【品名】(3,4-Diaminophenyl)phenylmethanone; 3,4-Diaminobenzophenone

【CA登记号】39070-63-8

【分子式】C₁₃H₁₂N₂O

【分子量】212.25116

【元素组成】C 73.57% H 5.7% N 13.2% O 7.54%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(V)

The acetylation of 4-aminobenzophenone (I) with acetic anhydride in hot benzene gives 4-acetamidobenzophenone (II), which is nitrated with 90% HNO3 in acetic acid-acetic anhydride yielding 4-acetamido-3-nitrobenzophenone (III). The hydrolysis of (III) with H2SO4 affords 4-amino-3-nitrobenzophenone (IV), which is reduced with H2 over Raney-Ni in THF to give 3,4-diaminobenzophenone (V). The cyclization of (V) with cyanogen bromide in methanol-water gives rise to 2-amino-5-benzoylbenzimidazol (VI), which is treated with isopropylsulfonyl chloride (A) and NaH in dimethoxyethane affording 2-amino-1-isopropylsulfonyl-6-benzoylbenzimidazol (VII). Finally, this compound is treated with hydroxylamine hydrochloride in refluxing methanol.

参考文献中间体

合成目标

【1】 Paget, C.J.; et al.; DE 2638551 .
【2】 Castaner, J.; Hopkins, S.J.; AR-336. Drugs Fut 1980, 5, 3, 120.

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)	18477	2-propanesulfonyl chloride	10147-37-2	C₃H₇ClO₂S	详情	详情
(I)	39112	3-Aminobenzophenone; (3-aminophenyl)(phenyl)methanone	2835-78-1	C₁₃H₁₁NO	详情	详情
(II)	39113	N-(3-benzoylphenyl)acetamide	58202-86-1	C₁₅H₁₃NO₂	详情	详情
(III)	39114	N-(5-benzoyl-2-nitrophenyl)acetamide		C₁₅H₁₂N₂O₄	详情	详情
(IV)	39115	(3-amino-4-nitrophenyl)(phenyl)methanone		C₁₃H₁₀N₂O₃	详情	详情
(V)	12830	(3,4-Diaminophenyl)phenylmethanone; 3,4-Diaminobenzophenone	39070-63-8	C₁₃H₁₂N₂O	详情	详情
(VI)	39116	(2-amino-1H-benzimidazol-6-yl)(phenyl)methanone		C₁₄H₁₁N₃O	详情	详情
(VII)	39117	[2-amino-1-(isopropylsulfonyl)-1H-benzimidazol-6-yl](phenyl)methanone		C₁₇H₁₇N₃O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The cyclization of 3,4-diaminobenzophenone (I) with acetylimidic acid ethyl ester (II) in refluxing methanol gives 5-benzoyl-2-methylbenzimidazole (III), which is reduced with NaBH4 in methanol yielding 5-(alpha-hydroxybenzyl)-2-methylbenzimidazole (IV). Finally, this compound is condensed with imidazole (V) in refluxing acetonitrile.

参考文献中间体

合成目标

【1】 Raeymaekers, A.H.M.; Freyne, E.J.E.; Sanz, G.C. (Janssen Pharmaceutica NV); Novel (1H-imidazol-1-ylmethyl) substd. benzimidazole derivs. AU 8778385; EP 0260744; JP 1989085975; US 4859684 .
【2】 Castaner, J.; Prous, J.; Irtemazole. Drugs Fut 1991, 16, 12, 1094.

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)	12830	(3,4-Diaminophenyl)phenylmethanone; 3,4-Diaminobenzophenone	39070-63-8	C₁₃H₁₂N₂O	详情	详情
(II)	12831	ethyl ethanimidoate	1000-84-6	C₄H₉NO	详情	详情
(III)	12832	(2-Methyl-1H-benzimidazol-5-yl)(phenyl)methanone		C₁₅H₁₂N₂O	详情	详情
(IV)	12833	(2-Methyl-1H-benzimidazol-5-yl)(phenyl)methanol		C₁₅H₁₄N₂O	详情	详情
(V)	10255	Imidazole; 1H-Imidazole	288-32-4	C₃H₄N₂	详情	详情

Extended Information