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【结 构 式】

【分子编号】53911

【品名】1-Methyl-1-phenylhydrazine; 1-Methylphenylhydrazine

【CA登记号】618-40-6

【 分 子 式 】C7H10N2

【 分 子 量 】122.16988

【元素组成】C 68.82% H 8.25% N 22.93%

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)

Treatment of 3-methoxy-2-cyclohexen-1-one (I) with n-butyllithium and diisopropylamine in THF, followed by addition of N,N-dimethylmethylene ammonium iodide (Eschenmoser's salt) (II) and precipitation with maleic acid, furnishes maleate (III). Methylation of (III) with iodomethane in DMF, followed by condensation with 2-methylimidazole (IV), affords compound (V), which is then converted into methylphenyl hydrazino derivative (VII) by first treatment with HCl in H2O followed by reaction with 1-methyl-1-phenylhydrazine (VI). Cyclization of (VII) is then performed by means of ZnCl2 in HOAc at 85 C to give carbazolone (VIII), and finally the target product is obtained by formation of the hydrochloride dihydrate salt.

1 Bell, J.A.; Ewan, G.B.; Oxford, A.W.; Humber, D.C.; Eldred, C.D.; Costes, I.H. (GlaxoSmithKline plc); Process for the preparation of 3-imidazolylmethyltetrahydrocarbazolones. EP 0219929 .
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) 53908 3-Methoxy-2-cyclohexen-1-one 16807-60-6 C7H10O2 详情 详情
(II) 48555 Eschenmoser's salt; N,N-Dimethylmethyleneimmonium chloride; N,N-Dimethylmethyleneimmonium iodide C3H8IN 详情 详情
(III) 55373   C14H21NO6 详情 详情
(IV) 15670 2-Methylimidazole; 2-Methyl-1H-imidazole 693-98-1 C4H6N2 详情 详情
(V) 53910 3-methoxy-6-[(2-methyl-1H-imidazol-1-yl)methyl]-2-cyclohexen-1-one C12H16N2O2 详情 详情
(VI) 53911 1-Methyl-1-phenylhydrazine; 1-Methylphenylhydrazine 618-40-6 C7H10N2 详情 详情
(VII) 53912 6-[(2-methyl-1H-imidazol-1-yl)methyl]-3-(2-methyl-2-phenylhydrazino)-2-cyclohexen-1-one n/a C18H22N4O 详情 详情
(VIII) 53903 9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one n/a C18H19N3O 详情 详情

合成路线2

该中间体在本合成路线中的序号:

2) Alkylation of the tetrahydropyridoindolone (VII) with 5-chloromethyl-4-methyloxazole (VIII) in dimethoxyethane in the presence of sodium hydride affords (IX). Ammonolysis of this material is carried out by heating with formamide.

1 Oxford, A.W.; Hagan, R.M.; Tyers, M.B.; Kilpatrick, G.J.; North, P.C.; GR-68755 Hydrochloride. Drugs Fut 1992, 17, 8, 660.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
53911 1-Methyl-1-phenylhydrazine; 1-Methylphenylhydrazine 618-40-6 C7H10N2 详情 详情
(V) 15737 dihydro-2,4(1H,3H)-pyridinedione C5H7NO2 详情 详情
(VI) 15738 4-[(Z)-methyl(phenyl)-lambda(5)-azanylidene]dihydro-2(1H,3H)-pyridinone C12H16N2O 详情 详情
(VII) 15739 5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one C12H12N2O 详情 详情
(VIII) 15740 5-(chloromethyl)-4-methyl-1,3-oxazole C5H6ClNO 详情 详情
(IX) 15741 5-methyl-2-[(4-methyl-1,3-oxazol-5-yl)methyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one C17H17N3O2 详情 详情
Extended Information