DMP-904, SP-904

N-(1-乙基丙基)-3-(4-甲氧基-2-甲基苯基)-2,5-二甲基吡唑并[1,5-A]嘧啶-7-胺Chemical Name: 7-(1-Ethylpropylamino)-3-(4-methoxy-2-methylphenyl)-2,5-dimethylpyrazolo[1,5-a]pyrimidine
CAS No. 202579-74-6
项目整合开发状态: Preclinical
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:The cyclization of 5-amino-4-(4-methoxy-2-methylphenyl)-3-methylpyrazole with ethyl acetoacetate (II) in refluxing acetic acid gives 7-hydroxy-3-(4-methoxy-2-methylphenyl)-5-methylpyrazolo[1,5-a]pyrimidine (III),which is treated with POCl3 and diethylaniline in refluxing toluene yielding the corresponding chloro derivative (IV).Finally,this compound is treated with pentyl-3-amine in DMSO at 150 C.

合成路线: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.