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【结 构 式】

【分子编号】20595

【品名】2-(3,4-dimethoxyphenyl)-N-[3-(2-iodo-5-methoxyphenyl)-1-methylpropyl]-N-methylacetamide

【CA登记号】

【 分 子 式 】C22H28INO4

【 分 子 量 】497.37313

【元素组成】C 53.13% H 5.67% I 25.51% N 2.82% O 12.87%

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:(VIII)

The condensation of 3-methoxybenzaldehyde (I) with acetone (II) by means of NaOH gives 1-(3-methoxyphenyl)-1-buten-3-one (III), which is hydrogenated with H2 over Pd/C in methanol yielding 1-(3-methoxyphenyl)-3-butanone (IV). The iodination of (IV) with I2-silver acetate in acetic acid affords 1-(2-iodo-5-methoxyphenyl)-3-butanone (V), which is reductocondensed with methylamine and sodium cyanoborohydride in methanol giving 2-iodo-5-methoxy-N,alpha-dimethylphenylpropanamine (VI). The acylation of (VI) with 3,4-dimethoxyphenylacetyl chloride (VII) by means of triethylamine in dichloromethane yields the corresponding acetamide (VIII), which is reduced with borane-THF complex affording the corresponding tertiary amine (IX), which is finally condensed with phenylacetylene (X) by means of butyllithium in THF.

1 Carson, J.R. (McNeilab, Inc.); Aralkyl(arylethynyl)aralkyl amines for use as vasodilators and antihypertensives. EP 0146271; ES 8604488; US 4661635 .
2 Prous, J.; Castaner, J.; McN-5691. Drugs Fut 1989, 14, 4, 322.
3 Carson, J.R.; Almond, H.R.; Brannan, M.D.; et al.; 2-Ethynylbenzenealkanamines. A new class of calcium entry blockers. J Med Chem 1988, 31, 3, 630-6.
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) 20589 3-methoxybenzaldehyde; m-Anisaldehyde 591-31-1 C8H8O2 详情 详情
(II) 23199 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one; Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether 67-64-1 C3H6O 详情 详情
(III) 20590 (E)-4-(3-methoxyphenyl)-3-buten-2-one C11H12O2 详情 详情
(IV) 20591 4-(3-methoxyphenyl)-2-butanone C11H14O2 详情 详情
(V) 20592 4-(2-iodo-5-methoxyphenyl)-2-butanone C11H13IO2 详情 详情
(VI) 20593 N-[3-(2-iodo-5-methoxyphenyl)-1-methylpropyl]-N-methylamine; 4-(2-iodo-5-methoxyphenyl)-N-methyl-2-butanamine C12H18INO 详情 详情
(VII) 20594 2-(3,4-dimethoxyphenyl)acetyl chloride C10H11ClO3 详情 详情
(VIII) 20595 2-(3,4-dimethoxyphenyl)-N-[3-(2-iodo-5-methoxyphenyl)-1-methylpropyl]-N-methylacetamide C22H28INO4 详情 详情
(IX) 20596 N-(3,4-dimethoxyphenethyl)-N-[3-(2-iodo-5-methoxyphenyl)-1-methylpropyl]-N-methylamine; N-(3,4-dimethoxyphenethyl)-4-(2-iodo-5-methoxyphenyl)-N-methyl-2-butanamine C22H30INO3 详情 详情
(X) 20597 1-ethynylbenzene 536-74-3 C8H6 详情 详情
Extended Information