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【结 构 式】

【药物名称】DPC-696, SK-696, DMP-696

【化学名称】8-(2,4-Dichlorophenyl)-N-[2-methoxy-1-(methoxymethyl)ethyl]-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-4-amine

【CA登记号】202578-52-7

【 分 子 式 】C18H21Cl2N5O2

【 分 子 量 】410.30637

【开发单位】Bristol-Myers Squibb (Originator)

【药理作用】Antidepressants, Anxiolytics, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, CRF1 Antagonists

合成路线1

Claisen condensation of 2,4-dichlorophenylacetonitrile (I) with ethyl acetate using of Na metal gave ketonitrile (II), which was reacted with hydrazine hydrate in the presence of AcOH to afford aminopyrazole (III). Subsequent condensation of (III) with ethyl acetimidate (IV) produced amidine (V). This was cyclized with diethyl carbonate and NaOEt to furnish the pyrazolotriazinone (VI). Chlorination of (VI) using phosphoryl chloride in N,N-dimethylaniline provided chloride (VII), which was finally coupled with 1,3-dimethoxy-2-aminopropane (VIII) to yield the title compound.

1 Gilligan, P.J.; He, L.; Zaczek, R.; et al.; 4-(1,3-Dimethoxyprop-2-ylamino)-2,7-dimethyl-8-(2,4-dichlorophenyl)pyrazolo[1,5-a]-1,3,5-triazine: A potent, orally bioavailable CRF1 receptor antagonist. J Med Chem 2000, 43, 3, 449.
2 Arvanitis, A.G.; Chorvat, R.J. (DuPont Pharmaceuticals Co.); Azolo triazines and pyrimidines. US 6124289; WO 9803510 .
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) 28484 2,4.Dichlorobenzyl cyanide; 2-(2,4-Dichlorophenyl)acetonitrile 6306-60-1 C8H5Cl2N 详情 详情
(II) 28485 2-(2,4-dichlorophenyl)-3-oxobutanenitrile C10H7Cl2NO 详情 详情
(III) 27688 4-(2,4-dichlorophenyl)-3-methyl-1H-pyrazol-5-amine C10H9Cl2N3 详情 详情
(IV) 12831 ethyl ethanimidoate 1000-84-6 C4H9NO 详情 详情
(V) 28486 N-[4-(2,4-dichlorophenyl)-3-methyl-1H-pyrazol-5-yl]ethanimidamide C12H12Cl2N4 详情 详情
(VI) 28487 8-(2,4-dichlorophenyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazin-4(3H)-one C13H10Cl2N4O 详情 详情
(VII) 28488 4-chloro-8-(2,4-dichlorophenyl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazine C13H9Cl3N4 详情 详情
(VIII) 23336 1,3-dimethoxy-2-propanamine C5H13NO2 详情 详情
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