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【结 构 式】

【分子编号】14618

【品名】2-chloro-4-methyl-3-pyridinamine; 2-chloro-4-methyl-3-pyridinylamine

【CA登记号】133627-45-9

【 分 子 式 】C6H7ClN2

【 分 子 量 】142.58776

【元素组成】C 50.54% H 4.95% Cl 24.86% N 19.65%

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 diazonium salt from 2-amino-4-methylpyridine (I) is converted to 2-hydroxy-4-methylpyridine (II), which is nitrated to give 2-hydroxy-4-methyl-3-nitropyridine (III). Conversion to 2-chloro-4-methyl-3-nitropyridine (IV) is effected with phosphorous oxychloride and phosphorous pentachloride. Reduction of (IV) with hydrogen/Raney Nickel provides 3-amino-2-chloro-4-methylpyridine (V), which is condensed with 2-chloronicotinoyl chloride to give 2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide (VI). Treatment with cyclopropylamine affords N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide (VII), which is cyclized in the presence of sodium hydride to yield nevirapine.

1 Hargrave, K.D.; Grozinger, K.G.; Proudfoot, J.R.; et al.; Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 1. Tricyclic pyridobenzo- and dipyridodiazepinones. J Med Chem 1991, 34, 7, 2231-41.
2 Riska, P.S.; Johnstone, J.N.; Silverstein, H.H.; Hattox, S.E.; Norris, S.H.; St. George, R.; Grob, P.M.; Hargrave, K.D.; Nevirapine. Drugs Fut 1992, 17, 10, 887.
3 Hargrave, K.D.; Merluzzi, V.J.; Labadia, M.; et al.; Inhibition of HIV-1 replication by a non-nucleoside reverse transcriptase inhibitor. Science 1990, 250, 4986, 1411-3.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
15224 2-chloronicotinoyl chloride 49609-84-9 C6H3Cl2NO 详情 详情
(I) 14614 2-Amino-4-picoline; 4-Methyl-2-pyridinamine; 4-Methyl-2-pyridinylamine; 2-Amino-4-methylpyridine 695-34-1 C6H8N2 详情 详情
(II) 14615 4-methyl-2-pyridinol C6H7NO 详情 详情
(III) 14616 4-Methyl-3-nitro-pyridin-2-ol; 4-Methyl-3-nitro-2-pyridinol 21901-18-8 C6H6N2O3 详情 详情
(IV) 14617 2-chloro-4-methyl-3-nitropyridine 23056-39-5 C6H5ClN2O2 详情 详情
(V) 14618 2-chloro-4-methyl-3-pyridinamine; 2-chloro-4-methyl-3-pyridinylamine 133627-45-9 C6H7ClN2 详情 详情
(VI) 14619 2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)nicotinamide C12H9Cl2N3O 详情 详情
(VII) 14620 N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)nicotinamide; N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide 133627-47-1 C15H15ClN4O 详情 详情
Extended Information