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【结 构 式】

【分子编号】34070

【品名】5-methyl-1H-imidazole

【CA登记号】822-36-6

【 分 子 式 】C4H6N2

【 分 子 量 】82.10512

【元素组成】C 58.52% H 7.37% N 34.12%
与该中间体有关的原料药合成路线共 4 条
合成路线1合成路线2合成路线3合成路线4

合成路线1

该中间体在本合成路线中的序号：(I)

1) By refluxing N-cyano-N',S-dimethylisoithiourea (B) and 5-methyl-4-[(2-aminoethyl)thiomethyl imidazol (III) in acetonitrile. The latter is prepared by reacting cysteamine (A) and 5-methyl-4-(hydroxymethyl)imidazol (II) (from 5-methylimidazol (I) and formalin) in acetic acid, in hydrochloric acid or in hydrobromic acid. 2) By reaction of 5-methyl-4-[(2-aminoethyl)thiomethyl]imidazol (III) with cyanodithioimido carbonic (C) acid dimethyl ester to give the isothiourea (IV), followed by reaction with methylamine. 3) By refluxing 1-methyl-3-[2-[[(5-methylimidazol-4-yl)-methyl]thio]ethyl]-2-thiourea (metiamide) (V) and lead cyanamide. The first is prepared by reaction of 5-methyl-4-[(2-aminoethyl)thiomethyl]imidazol (III) with methyl isocyanate (D).

参考文献 中间体
合成目标
【1】 Durant, G.J.; et al.; Pharmacologically active guanidine compounds. DE 2211454; DE 2265369; FR 2128505; GB 1338169; US 3950333 .
【2】 Erlenmeyer, H.; et al.; Helv Chim Acta 1948, 31, 32.
【3】 Durant, G.J.; et al.; Certain N-cyanoguanidines. DE 2344779; FR 2199467; GB 1397436; JP 49075574; US 3876647 .
【4】 Castaner, J.; Cimetidine. Drugs Fut 1976, 1, 1, 13.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(D) 12092 Methyl isothiocyanate; MITC; (Methylimino)(thioxo)methane 556-61-6 C2H3NS 详情 详情
(A) 13186 2-Aminoethanethiol; 2-Amino-1-ethanethiol; 2-Aminoethylhydrosulfide; Cysteamine 60-23-1 C2H7NS 详情 详情
(B) 34072 [[(E)-(methylamino)(methylsulfanyl)methylidene]amino](nitrilo)methane C4H7N3S 详情 详情
(I) 34070 5-methyl-1H-imidazole 822-36-6 C4H6N2 详情 详情
(II) 14216 (5-Methyl-1H-imidazol-4-yl)methanol 29636-87-1 C5H8N2O 详情 详情
(III) 34071 2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl]-1-ethanamine; 2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl]ethylamine C7H13N3S 详情 详情
(IV) 34073 4-[[(2-[[(cyanoimino)(methylsulfanyl)methyl]amino]ethyl)sulfanyl]methyl]-5-methyl-1H-imidazole C10H15N5S2 详情 详情
(V) 34074 N-methyl-N'-(2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl]ethyl)thiourea C9H16N4S2 详情 详情
(C) 18174 [[bis(methylsulfanyl)methylene]amino](nitrilo)methane 10191-60-3 C4H6N2S2 详情 详情

合成路线2

该中间体在本合成路线中的序号：(II)

　

参考文献 中间体
合成目标
【1】 Abel S, Acemoglu M, Erb B, et al. 2008. Process for the synthesis of organic compounds. US 20080200692A1.
【2】 Wang YL. Li J, Kansal VK, et al. 2010. Nilotinib intermediates and preparation thereof. US 20100016590A1.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
（X） 67346 (Z)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 　 C10H12N2O 详情 详情
(I) 67340 3-fluoro-5-(trifluoromethyl)benzonitrile 149793-69-1 C8H3F4N 详情 详情
(II) 34070 5-methyl-1H-imidazole 822-36-6 C4H6N2 详情 详情
(III) 67341 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzonitrile 　 C12H8F3N3 详情 详情
(IV) 67342 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid 　 C12H9F3N2O2 详情 详情
(V) 67343 tert-butyl (3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)carbamate 　 C16H18F3N3O2 详情 详情
(VI) 67344 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline 641571-11-1 C11H10F3N3 详情 详情
(VII) 38737 ethyl 4-amino-3-methylbenzoate 40800-65-5 C10H13NO2 详情 详情
(VIII) 67345 ethyl 3-guanidino-4-methylbenzoate 　 C11H15N3O2 详情 详情
(IX) 12027 1-(3-Pyridinyl)-1-ethanone; 1-(3-Pyridinyl)ethanone 350-03-8 C7H7NO 详情 详情
(XI) 67347 ethyl 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoate 641569-97-3 C19H18N4O2 详情 详情
(XII) 67348 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid 641569-94-0 C17H14N4O2 详情 详情

合成路线3

该中间体在本合成路线中的序号：(IX)

　

参考文献 中间体
合成目标
【1】 Wang YL. Li J, Kansal VK, et al. 2010. Nilotinib intermediates and preparation thereof. WO 2010009402A9.
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) 38737 ethyl 4-amino-3-methylbenzoate 40800-65-5 C10H13NO2 详情 详情
(II) 67345 ethyl 3-guanidino-4-methylbenzoate 　 C11H15N3O2 详情 详情
(III) 12027 1-(3-Pyridinyl)-1-ethanone; 1-(3-Pyridinyl)ethanone 350-03-8 C7H7NO 详情 详情
(IV) 67346 (Z)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 　 C10H12N2O 详情 详情
(V) 67347 ethyl 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoate 641569-97-3 C19H18N4O2 详情 详情
(VI) 67348 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid 641569-94-0 C17H14N4O2 详情 详情
(VII) 51493 3-Amino-5-bromobenzotrifluoride 54962-75-3 C7H5BrF3N 详情 详情
(VIII) 67349 N-(3-bromo-5-(trifluoromethyl)phenyl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide 　 C24H17BrF3N5O 详情 详情
(IX) 34070 5-methyl-1H-imidazole 822-36-6 C4H6N2 详情 详情

合成路线4

该中间体在本合成路线中的序号：(VI)

　

参考文献 中间体
合成目标
【1】 Huang WS, Shakespeare WC. 2007. An efficient synthesis of nilotinib (AMN107). Synthesis, 14: 2121～2124.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
（XI） 67344 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline 641571-11-1 C11H10F3N3 详情 详情
(I) 67350 ethyl 4-amino-3-methylbenzoate 　 C10H13NO2 详情 详情
(II) 67345 ethyl 3-guanidino-4-methylbenzoate 　 C11H15N3O2 详情 详情
(III) 47516 (E)-3-(dimethylamino)-1-(3-pyridinyl)-2-propen-1-one 123367-26-0 C10H12N2O 详情 详情
(IV) 67347 ethyl 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoate 641569-97-3 C19H18N4O2 详情 详情
(V) 67340 3-fluoro-5-(trifluoromethyl)benzonitrile 149793-69-1 C8H3F4N 详情 详情
(VI) 34070 5-methyl-1H-imidazole 822-36-6 C4H6N2 详情 详情
(VII) 67341 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzonitrile 　 C12H8F3N3 详情 详情
(VIII) 67342 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid 　 C12H9F3N2O2 详情 详情
(IX) 67343 tert-butyl (3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)carbamate 　 C16H18F3N3O2 详情 详情
(X) 67348 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid 641569-94-0 C17H14N4O2 详情 详情
Extended Information