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【结 构 式】

【分子编号】23564

【品名】1-methyl-3-oxo-7-(4-pyridinyl)-2,3,5,6,7,8-hexahydro-4-isoquinolinecarbonitrile

【CA登记号】

【 分 子 式 】C16H15N3O

【 分 子 量 】265.31472

【元素组成】C 72.43% H 5.7% N 15.84% O 6.03%

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:(X)

This compound can be prepared by several different ways: 1) The reaction ot 4-(chloromethyl)pyridine (I) with NaCN in toluene - water gives 4-(cyanomethyl)pyridine (II), which is condensed with methyl acrylate (III) yielding dimethyl 4-cyano 4-(4-pyridyl)pimelate (IV). The hydrolysis and decarboxylation of (IV) atfords 4-(4-pyridyl)pimelic acid (V), which is cyclized by means of potassium tert-butoxide giving 4-(4-pyridyl)cyclohexanone (VI). The acetylation of (VI) with acetic anhydride or acetylimidazole affords 2-acetyl(4-4 pyridyl)cyclohexanone (VII), which is finally cyclized with acetylacetamide (VIII) by means of dimethylamine. 2) The cyclization of (VII) with cyanoacetamide (IX) by means of piperidine gives 4-cyano-1-methyl-7-(4-pyridyl)-5,6,7,8-tetrahydro-3(2H)-isoquinolinone (X), which is finally treated with methyl magnesium iodide in ether. 3) The condensation of 4 bromopyridine (XI) and cyclohexanedione monoethyleneketal (XII) by means of butyllithium in THF gives 4-hydroxy-4-(4-pyridyil)cyclohexanone ethyleneketal (XIII), which is dehydrated by treatment with SOCl2 and then with NaOH to afford 4-(4-pyridyl)-3-cyclohexenone ethyleneketal (XIV). Finally, this compound is hydrolyzed with HCl and reduced with H2 over Pd/C in 0.5 N HCl yielding cyclohexanone (VII), already obtained.

1 Hirayama, M.; Ito, T.; Kitano, T.; Maruyama, M.; Otsuka, K.; Sannohe, K. (Mitsui Chemicals, Inc.); Isoquinoline derivs.. EP 0207500; US 4639521 .
2 Fukazawa, N.; Kaiho, T.; Yamashita, H. (Mitsui Chemicals, Inc.); Process for preparing 4-acetyl isoquinolinone cpds. JP 1987187467; US 4814458 .
3 Prous, J.; Castaner, J.; MS-857. Drugs Fut 1988, 13, 9, 831.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10158 Piperidine 110-89-4 C5H11N 详情 详情
(I) 10844 4-(Chloromethyl)pyridine 10445-91-7 C6H6ClN 详情 详情
(II) 23556 2-(4-pyridinyl)acetonitrile C7H6N2 详情 详情
(III) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(IV) 23558 dimethyl 4-cyano-4-(4-pyridinyl)heptanedioate C15H18N2O4 详情 详情
(V) 23559 4-(4-pyridinyl)heptanedioic acid C12H15NO4 详情 详情
(VI) 23560 4-(4-pyridinyl)cyclohexanone C11H13NO 详情 详情
(VII) 23561 2-acetyl-4-(4-pyridinyl)cyclohexanone C13H15NO2 详情 详情
(VIII) 23562 3-oxobutanamide 5977-14-0 C4H7NO2 详情 详情
(IX) 12122 Cyanoacetamide; 2-Cyanoacetamide 107-91-5 C3H4N2O 详情 详情
(X) 23564 1-methyl-3-oxo-7-(4-pyridinyl)-2,3,5,6,7,8-hexahydro-4-isoquinolinecarbonitrile C16H15N3O 详情 详情
(XI) 23565 4-bromopyridine 1120-87-2 C5H4BrN 详情 详情
(XII) 11377 1,4-Dioxaspiro[4.5]decan-8-one 4746-97-8 C8H12O3 详情 详情
(XIII) 23567 8-(4-pyridinyl)-1,4-dioxaspiro[4.5]decan-8-ol C13H17NO3 详情 详情
(XIV) 23568 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine C13H15NO2 详情 详情
Extended Information