• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】58178

【品名】ethyl 3-({[1-formyl-2-(methyl{2-[(3-methylbenzyl)amino]ethyl}amino)ethyl]amino}carbonyl)-1H-indazole-1-carboxylate

【CA登记号】

【 分 子 式 】C25H31N5O4

【 分 子 量 】465.55244

【元素组成】C 64.5% H 6.71% N 15.04% O 13.75%

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 reductocondensation of ethanolamine (I) with 3-methylbenzaldehyde (II) by means of NaBH4 gives N-(3-methylbenzyl)ethanolamine (III), which is treated with SOCl2 to yield the 2-chloroethyl derivative (IV). The reaction of (IV) with methylamine (V) affords N-methyl-N'-(3-methylbenzyl)ethane-1,2-diamine (VI), which is condensed with the pyrazole-carboxamide derivative (VII) to provide the unstable compound (VIII)?? (IX). The reduction of (IX) with NaBH4 gives the racemic amide (X), which is submitted to optical resolution by preferential crystallization to yield the (R)-isomer (XI) (1,2). The hydrogenation of (XI) with H2 over Pd/C in ethanol affords the debenzylated compound (XII), which is alkylated by reductocondensation with acetaldehyde (XIII) and NaBH4 in methanol to provide the chiral N-(1-ethyl-4'-methylperhydro-1,4-diazepin-6-(R)-yl)-1H-pyrazole-3-carboxamide (XIV). Finally, this compound is treated with refluxing aqueous HCl to give the corresponding 6(R)-amino derivative (XV).

2 Hirokawa, Y.; et al.; Synthesis and structure-activity relationships of 4-amino-5-chloro-N-(1,4-dialkylhexahydro-1,4-diazepin-6-yl)-2-methoxybenzamide derivatives, novel and potent serotonin 5-HT3 and dopamine D2 receptors dual antagonist. Chem Pharm Bull 2002, 50, 7, 941.
1 Harada, H.; et al.; Synthesis and resolution of (±)-N-[1-methyl-4-(3-methylbenzyl)hexahydro-1H-1,4-diazepin-6-yl]-1H-indazole-3-carboxamide by preferential crystallization. Tetrahedron Asymmetry 1997, 8, 14, 2367.
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) 10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
(II) 41077 3-methylbenzaldehyde 620-23-5 C8H8O 详情 详情
(III) 58175 2-[(3-methylbenzyl)amino]-1-ethanol C10H15NO 详情 详情
(IV) 58176 2-chloro-N-(3-methylbenzyl)-1-ethanamine; N-(2-chloroethyl)-N-(3-methylbenzyl)amine C10H14ClN 详情 详情
(V) 11021 Methanamine; Methylamine 74-89-5 CH5N 详情 详情
(VI) 54009 N~1~-methyl-N~2~-(3-methylbenzyl)-1,2-ethanediamine; N-methyl-N-{2-[(3-methylbenzyl)amino]ethyl}amine n/a C11H18N2 详情 详情
(VII) 58177 ethyl 3-{[(1-formylvinyl)amino]carbonyl}-1H-indazole-1-carboxylate C14H13N3O4 详情 详情
(VIII) 58178 ethyl 3-({[1-formyl-2-(methyl{2-[(3-methylbenzyl)amino]ethyl}amino)ethyl]amino}carbonyl)-1H-indazole-1-carboxylate C25H31N5O4 详情 详情
(IX) 58179 6-({[1-(ethoxycarbonyl)-1H-indazol-3-yl]carbonyl}amino)-4-methyl-1-(3-methylbenzyl)-3,4,5,6-tetrahydro-2H-1,4-diazepin-1-ium C25H30N5O3 详情 详情
(X) 58180 N-[1-methyl-4-(3-methylbenzyl)-1,4-diazepan-6-yl]-1H-indazole-3-carboxamide C22H27N5O 详情 详情
(XI) 58181 N-[(6S)-1-methyl-4-(3-methylbenzyl)-1,4-diazepan-6-yl]-1H-indazole-3-carboxamide C22H27N5O 详情 详情
(XII) 58182 N-[(6S)-1-methyl-1,4-diazepan-6-yl]-1H-indazole-3-carboxamide C14H19N5O 详情 详情
(XIII) 11974 Acetaldehyde 75-07-0 C2H4O 详情 详情
(XIV) 58183 N-[(6S)-1-ethyl-4-methyl-1,4-diazepan-6-yl]-1H-indazole-3-carboxamide C16H23N5O 详情 详情
(XV) 17802 (6S)-1-ethyl-4-methyl-1,4-diazepan-6-ylamine; (6S)-1-ethyl-4-methyl-1,4-diazepan-6-amine C8H19N3 详情 详情
Extended Information