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【结 构 式】

【分子编号】54259

【品名】2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-amine; 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-ylamine

【CA登记号】n/a

【 分 子 式 】C13H16N2O

【 分 子 量 】216.28292

【元素组成】C 72.19% H 7.46% N 12.95% O 7.4%

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 intermediate 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-amine (IV) has been obtained by two different ways: The cyclization of the bicyclic isatin (I) with cyclohexanone, NH4OH and NH4OAc in methanol gives 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-carboxamide (III), which is submitted to a Hofmann rearrangement by means of Br2 and NaOH in water to yield the intermediate amine (IV). The cyclization of 2-amino-4,5-dimethylfuran-3-carbonitrile (V) with cyclohexanone (II) by means of ZnCl2 in hot xylene or nitrobenzene gives directly the intermediate amine (IV). Finally, amine (IV) is condensed with 2-(2-oxopyrrolidin-1-yl)acetic acid methyl ester (VI) by means of NaH in NMP to provide the target amide.

1 Chaki, H.; et al.; Design and syntheses of 4-acylaminopyridine derivatives: Novel high affinity choline uptake enhancers II. Bioorg Med Chem Lett 1995, 5, 14, 1495.
2 Ninomiya, K.; Saito, K.; Sugano, M.; Tobe, A.; Morinaka, Y.; Bessho, T.; Harada, H. (Mitsubishi Chemical Corp.); 4-Acylaminopyridine derivs.. EP 0427636; JP 1991151366; JP 1991218360; JP 1991218361; US 5397785; US 5536728; US 5861411 .
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) 54257 2,3-dimethyl-6,6a-dihydro-3aH-furo[2,3-b]pyrrole-4,5-dione n/a C8H9NO3 详情 详情
(II) 11059 Cyclohexanone 108-94-1 C6H10O 详情 详情
(III) 54258 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinoline-4-carboxamide n/a C14H16N2O2 详情 详情
(IV) 54259 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-amine; 2,3-dimethyl-5,6,7,8-tetrahydrofuro[2,3-b]quinolin-4-ylamine n/a C13H16N2O 详情 详情
(V) 54260 2-Amino-4,5-dimethylfuran-3-carbonitrile 5117-88-4 C7H8N2O 详情 详情
(VI) 16475 Methyl 2-oxo-1-pyrrolidineacetate; Methyl 2-(2-oxo-1-pyrrolidinyl)acetate 59776-88-4 C7H11NO3 详情 详情
Extended Information