methyl 3-amino-4-[[bis(4-propylphenyl)methyl]amino]benzoate -Drug Synthesis Database

【结构式】

【分子编号】21937

【品名】methyl 3-amino-4-[[bis(4-propylphenyl)methyl]amino]benzoate

【CA登记号】

【分子式】C₂₇H₃₂N₂O₂

【分子量】416.56336

【元素组成】C 77.85% H 7.74% N 6.72% O 7.68%

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：(IV)

The condensation of methyl 4-chloro-3-nitrobenzoate (I) with dipropylbenzhydryl amine (II), followed by reduction of the nitro group of the resulting (III) with H2 in the presence of PtO2 yielded diamine (IV). Treatment of (IV) with triethyl orthoformate and formic acid at 120 C produced the benzimidazole (V), which was hydrolyzed with NaOH to the benzimidazolecarboxylic (VI). Finally, acid (VI) was condensed with aniline (VII) using 2-chloro-1-methylpyridinium iodide (CMP) and Bu3N to furnish the target amide.

参考文献中间体

合成目标

【1】 Takami, H.; Kishibayashi, N.; Ishii, A.; Kumazawa, T.; Indole and benzimidazole derivatives as steroid 5alpha-reductase inhibitors in the rat prostate. Bioorg Med Chem 1998, 6, 12, 2441.

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)	21934	methyl 4-chloro-3-nitrobenzoate	14719-83-6	C₈H₆ClNO₄	详情	详情
(II)	21935	bis(4-propylphenyl)methanamine; bis(4-propylphenyl)methylamine		C₁₉H₂₅N	详情	详情
(III)	21936	N-[4-(methoxymethyl)-2-nitrophenyl]-N-[phenyl(4-propylphenyl)methyl]amine; 4-(methoxymethyl)-2-nitro-N-[phenyl(4-propylphenyl)methyl]aniline		C₂₄H₂₆N₂O₃	详情	详情
(IV)	21937	methyl 3-amino-4-[[bis(4-propylphenyl)methyl]amino]benzoate		C₂₇H₃₂N₂O₂	详情	详情
(V)	21938	methyl 1-[bis(4-propylphenyl)methyl]-1H-benzimidazole-5-carboxylate		C₂₈H₃₀N₂O₂	详情	详情
(VI)	21939	1-[bis(4-propylphenyl)methyl]-1H-benzimidazole-5-carboxylic acid		C₂₇H₂₈N₂O₂	详情	详情
(VII)	21940	ethyl 4-(2-aminophenoxy)butanoate		C₁₂H₁₇NO₃	详情	详情

Extended Information