• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】46877

【品名】N-(2-amino-5-methoxyphenyl)-N-methylamine; 4-methoxy-N(2)-methyl-1,2-benzenediamine

【CA登记号】

【 分 子 式 】C8H12N2O

【 分 子 量 】152.19616

【元素组成】C 63.13% H 7.95% N 18.41% O 10.51%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VI)

The intermediate phenylenediamine (VI) was prepared as follows. Reaction of 5-chloro-2-nitroaniline (I) with sodium methoxide afforded 5-methoxy-2-nitroaniline (II), which was subsequently converted to the N-Boc derivative (III). Methylation of (III) with iodomethane and NaH, followed by acidic treatment of the resulting N-methyl carbamate (IV), produced the N-methyl aniline (V). The nitro group of (V) was then reduced with the combination SnCl2-NaBH4 to furnish the diamine (VI).

1 Fujita, T.; Wada, K.; Oguchi, M.; Yanagisawa, H.; Fujimoto, K.; Fujiwara, T.; Horikoshi, H.; Yoshioka, T. (Sankyo Co., Ltd.); Benzimidazole derivs., their preparation and their therapeutic use. CA 2177858; EP 0745600; JP 1997295970; JP 2000001487; US 5886014 .
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) 15709 5-chloro-2-nitrophenylamine; 5-chloro-2-nitroaniline 1635-61-6 C6H5ClN2O2 详情 详情
(II) 42920 5-methoxy-2-nitrophenylamine; 5-methoxy-2-nitroaniline 16133-49-6 C7H8N2O3 详情 详情
(III) 46874 tert-butyl 5-methoxy-2-nitrophenylcarbamate C12H16N2O5 详情 详情
(IV) 46875 tert-butyl 5-methoxy-2-nitrophenyl(methyl)carbamate C13H18N2O5 详情 详情
(V) 46876 5-methoxy-N-methyl-2-nitroaniline; N-(5-methoxy-2-nitrophenyl)-N-methylamine C8H10N2O3 详情 详情
(VI) 46877 N-(2-amino-5-methoxyphenyl)-N-methylamine; 4-methoxy-N(2)-methyl-1,2-benzenediamine C8H12N2O 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VI)

Alkylation of 5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione (VII) with methyl bromoacetate (VIII) in the presence of cesium carbonate gave rise to the aryloxy acetate (IX). Subsequent cleavage of the N-trityl protecting group of (IX) was achieved by treatment with HOAc in aqueous dioxan at 80 C. The resulting ester (X) was finally condensed with phenylenediamine (VI) to produce the target benzimidazole.

2 Fujita, T.; Fujiwara, T.; Izumi, T. (Sankyo Co., Ltd.); Hydrochloride of fused-heterocycle cpd.. EP 1180519; JP 2001039976; US 2002111373; WO 0071540 .
1 Fujita, T.; Wada, K.; Oguchi, M.; Yanagisawa, H.; Fujimoto, K.; Fujiwara, T.; Horikoshi, H.; Yoshioka, T. (Sankyo Co., Ltd.); Benzimidazole derivs., their preparation and their therapeutic use. CA 2177858; EP 0745600; JP 1997295970; JP 2000001487; US 5886014 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 46877 N-(2-amino-5-methoxyphenyl)-N-methylamine; 4-methoxy-N(2)-methyl-1,2-benzenediamine C8H12N2O 详情 详情
(VII) 18803 5-(4-hydroxybenzyl)-3-trityl-1,3-thiazolidine-2,4-dione C29H23NO3S 详情 详情
(VIII) 12309 methyl 2-bromoacetate; methyl bromoacetate 96-32-2 C3H5BrO2 详情 详情
(IX) 46878 methyl 2-[4-[(2,4-dioxo-3-trityl-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate C32H27NO5S 详情 详情
(X) 46879 methyl 2-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]acetate C13H13NO5S 详情 详情
Extended Information