SCH-79797, -Drug Synthesis Database

【结构式】

【药物名称】SCH-79797

【化学名称】N3-Cyclopropyl-7-(4-isopropylbenzyl)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamine

【CA登记号】245520-69-8

【分子式】C₂₃H₂₅N₅

【分子量】371.4892

【开发单位】Schering-Plough (Originator)

【药理作用】Antiplatelet Therapy, CARDIOVASCULAR DRUGS, Coagulation Disorders Therapy, HEMATOLOGIC DRUGS, Restenosis Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, PAR1 Antagonists

合成路线1

Alkylation of 5-nitroindole (I) with 4-isopropylbenzyl chloride (II) in the presence of Cs2CO3 provided the N-benzylindole derivative (III). Reduction of the nitro group of (III) by hydrogenation over Pd/C gave the corresponding amine, which was isolated as the hydrochloride salt (IV). The required pyrroloquinazoline system (V) was then prepared by reaction of (IV) with trichloromethyl isocyanate, followed by treatment with POCl3. Displacement of the 1-chlorine of (V) by ammonia afforded amine (VI). The remaining 3-chlorine of (VI) was then displaced by cyclopropylamine (VII) to furnish the title compound.

参考文献中间体

【1】 Boykow, G.; Ahn, H.-S.; Arik, L.; et al.; Structure-activity relationships of pyrroloquinazolines as thrombin receptor antagonists. Bioorg Med Chem Lett 1999, 9, 14, 2073.

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)	26916	5-Nitroindole; 5-nitro-1H-indole	6146-52-7	C₈H₆N₂O₂	详情	详情
(II)	33769	1-(chloromethyl)-4-isopropylbenzene	2051-18-5	C₁₀H₁₃Cl	详情	详情
(III)	33770	1-(4-isopropylbenzyl)-5-nitro-1H-indole		C₁₈H₁₈N₂O₂	详情	详情
(IV)	33771	1-(4-isopropylbenzyl)-1H-indol-5-amine; 1-(4-isopropylbenzyl)-1H-indol-5-ylamine		C₁₈H₂₀N₂	详情	详情
(V)	33772	1,3-dichloro-7-(4-isopropylbenzyl)-7H-pyrrolo[3,2-f]quinazoline		C₂₀H₁₇Cl₂N₃	详情	详情
(VI)	33773	3-chloro-7-(4-isopropylbenzyl)-7H-pyrrolo[3,2-f]quinazolin-1-ylamine; 3-chloro-7-(4-isopropylbenzyl)-7H-pyrrolo[3,2-f]quinazolin-1-amine		C₂₀H₁₉ClN₄	详情	详情
(VII)	12263	Cyclopropylamine; Cyclopropanamine	765-30-0	C₃H₇N	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(2)