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【结 构 式】

【药物名称】CL-329167

【化学名称】2-Butyl-6-(1-methoxy-1-methylethyl)-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]quinazolin-4(3H)-one

【CA登记号】143945-39-5, 144364-95-4 (Na salt)

【 分 子 式 】C30H32N6O2

【 分 子 量 】508.62854

【开发单位】Wyeth Pharmaceuticals (Originator)

【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Angiotensin AT1 Antagonists

合成路线1

The cyclization of 2-amino-5-iodobenzoic acid (I) with pentanoic anhydride (II) in basic medium gives 2-butyl-6-iodoquinazolin-4(3H)-one (III), which is condensed with CO and methanol by means of PdCl2(PPh3)2 and TEA yielding 2-butyl-4-oxo-3,4-dihydroquinazoline-6-carboxylic acid methyl ester (IV). The Grignard condensation of (IV) with methylmagnesium bromide affords the tertiary alcohol (V), which is finally condensed with the tetrazolylbiphenyl (VI) by means of LiOMe, methylated at the tertiary alcohol with methyl iodide and NaH, and deprotected with NaOH in methanol/THF.

1 Levin, J.I.; Chen, P.S.; Porter, R.S.; 2,3,6-Substituted quinazolinones as angiotensin II receptor antagonists. Drugs Fut 1995, 20, 1, 55.
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) 19964 5-Iodoanthranilic acid; 2-amino-5-iodobenzoic acid 5326-47-6 C7H6INO2 详情 详情
(II) 27683 pentanoic anhydride 2082-59-9 C10H18O3 详情 详情
(III) 41190 2-butyl-6-iodo-4(3H)-quinazolinone C12H13IN2O 详情 详情
(IV) 41191 methyl 2-butyl-4-oxo-3,4-dihydro-6-quinazolinecarboxylate C14H16N2O3 详情 详情
(V) 41192 2-butyl-6-(1-hydroxy-1-methylethyl)-4(3H)-quinazolinone C15H20N2O2 详情 详情
(VI) 15538 5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-trityl-2H-1,2,3,4-tetraazole 124750-51-2 C33H25BrN4 详情 详情
Extended Information