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【结 构 式】

【分子编号】52620

【品名】N~1~-{3-[2,6-dichloro-4-(methyloxy)phenyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl}-1,2-ethanediamine

【CA登记号】

【 分 子 式 】C17H19Cl2N5O

【 分 子 量 】380.27636

【元素组成】C 53.69% H 5.04% Cl 18.65% N 18.42% O 4.21%

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:(XI)

The reaction of 2,6-dichloro-4-methoxybenzyl chloride (I) with tetraethylammonium cyanide in refluxing dichloromethane gives 2-(2,6-dichloro-4-methoxyphenyl)acetonitrile (II), which is condensed with ethyl acetate (III) by means of sodium ethoxide in refluxing ethanol to yield the 3-oxobutyronitrile (IV). The cyclization of (IV) with hydrazine (V) by means of HOAc in refluxing benzene affords the aminopyrazole (VI), which is further cyclized with ethyl acetoacetate (VII) in refluxing acetic acid to provide 3-(2,6-dichloro-4-methoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol (VIII). The reaction of (VIII) with refluxing POCl3 furnishes the corresponding chloro derivative (IX), which is allowed to react with ethylenediamine (X) in hot acetonitrile to give 7-(2-aminoethylamino)-3-(2,6-dichloro-4-methoxyphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine (XI). Finally, this compound is reductocondensed with tetrahydropyran-4-one (XII) by means of sodium cyanoborohydride in methanol/HOAc to yield the target CP-671906-01.

1 Giangiordano, M.; Tran, J.; Darrow, J.W.; De Lombaert, S.; Blum, C.; Griffith, D.A.; Carpino, P.A. (Neurogen Corp.; Pfizer Inc.); Certain alkylene diamine-substd. pyrazolo[1,5-a]-1,5-pyrimidines and pyrazolo[1,5-a]-1,3,5-triazines. US 6372743; WO 0123387 .
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) 52615 3,5-dichloro-4-(chloromethyl)phenyl methyl ether; 1,3-dichloro-2-(chloromethyl)-5-(methyloxy)benzene C8H7Cl3O 详情 详情
(II) 52616 2-[2,6-dichloro-4-(methyloxy)phenyl]acetonitrile C9H7Cl2NO 详情 详情
(III) 17491 ethyl acetate 141-78-6 C4H8O2 详情 详情
(IV) 52621 2-[2,6-dichloro-4-(methyloxy)phenyl]-3-oxobutanenitrile C11H9Cl2NO2 详情 详情
(V) 27344 hydrazine 302-01-2 H4N2 详情 详情
(VI) 52617 4-[2,6-dichloro-4-(methyloxy)phenyl]-3-methyl-1H-pyrazol-5-amine; 4-[2,6-dichloro-4-(methyloxy)phenyl]-3-methyl-1H-pyrazol-5-ylamine C11H11Cl2N3O 详情 详情
(VII) 11819 ethyl acetoacetate; ethyl 3-oxobutanoate;Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate 141-97-9 C6H10O3 详情 详情
(VIII) 52618 3-[2,6-dichloro-4-(methyloxy)phenyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol C15H13Cl2N3O2 详情 详情
(IX) 52619 7-chloro-3-[2,6-dichloro-4-(methyloxy)phenyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidine; 3,5-dichloro-4-(7-chloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)phenyl methyl ether C15H12Cl3N3O 详情 详情
(X) 14754 ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine;1,2-Ethanediamine 107-15-3 C2H8N2 详情 详情
(XI) 52620 N~1~-{3-[2,6-dichloro-4-(methyloxy)phenyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-yl}-1,2-ethanediamine C17H19Cl2N5O 详情 详情
(XII) 31563 tetrahydro-4H-pyran-4-one 29943-42-8 C5H8O2 详情 详情
Extended Information