• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】36442

【品名】2-[mesityl(methyl)amino]-9,10-dimethoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one

【CA登记号】

【 分 子 式 】C24H27N3O3

【 分 子 量 】405.4968

【元素组成】C 71.09% H 6.71% N 10.36% O 11.84%

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:(VII)

HL-725 has been synthesized in a variety of ways: 1) 1-Carbamoylmethylene-6,7-methoxy-1,2,3,4-tetrahydroisoquinoline (I) was cyclized on treatment with diethylcarbonate (A) to give 9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinoline-2,4-dione (II). Methylation of (II) with methyliodide in dimethylformamide in the presence of sodium hydride afforded (III). The N-methyl compound (III) was treated with phosphorous pentasulfide to give the thio compound (IV). Reaction of (IV) with mesidine (C) afforded HL-725. 2) Alternately, the compound (II) was reacted with phosphorous oxychloride to yield the chloro compound (V), which was then reacted with mesidine to give the mesitylino derivative (VI). Methylation of (VI) with methyliodide afforded HL-725 and the exo-N-methyl isomer (VII), which were separated chromatographcally. 3) 3,4-Dimethoxy-beta-phenethyl bromide (VIII) was reacted with barbituric acid (B) to give the alkylated product (IX). Bischler-Napieralski-type cyclization afforded (II), which was then converted to HL-725 by the appropriate route.

1 DE 2720085 .
2 Lal, B.; D'Sa, A.; 33rd Ind Pharm Cong (Dec 21, Jaipur) 1981, 16, Suppl. 1.
3 de Souza, N.J.; Dadkar, N.K.; Lal, B.; D'Sa, A.; Dohadwalla, A.N.; Trequinsin, a potent antihypertensive vasodilator in the series of 2-(arylimino)-3-alkyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido-[6,1-a]isoquinolin-4-ones. J Med Chem 1984, 27, 1470-80.
4 Sas, G.; Blasko, G.; Trequinsin and its analogs. Drugs Fut 1989, 14, 11, 1083-91.
5 Arya, V.P.; HL-725. Drugs Fut 1982, 7, 6, 390.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 17470 diethyl carbonate; diethylcarbonate 105-58-8 C5H10O3 详情 详情
(B) 36445 2,4,6(1H,3H,5H)-pyrimidinetrione 67-52-7 C4H4N2O3 详情 详情
(I) 36436 2-[6,7-dimethoxy-3,4-dihydro-1(2H)-isoquinolinylidene]acetamide C13H16N2O3 详情 详情
(II) 36437 9,10-dimethoxy-6,7-dihydro-2H-pyrimido[6,1-a]isoquinoline-2,4(3H)-dione C14H14N2O4 详情 详情
(III) 36438 9,10-dimethoxy-3-methyl-6,7-dihydro-2H-pyrimido[6,1-a]isoquinoline-2,4(3H)-dione C15H16N2O4 详情 详情
(IV) 36439 9,10-dimethoxy-3-methyl-2-thioxo-2,3,6,7-tetrahydro-4H-pyrimido[6,1-a]isoquinolin-4-one C15H16N2O3S 详情 详情
(V) 36440 2-chloro-9,10-dimethoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one C14H13ClN2O3 详情 详情
(VI) 36441 2-(mesitylamino)-9,10-dimethoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one C23H25N3O3 详情 详情
(VII) 36442 2-[mesityl(methyl)amino]-9,10-dimethoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one C24H27N3O3 详情 详情
(VIII) 36443 1-(3,4-dimethoxyphenyl)-2-bromoenthane C10H13BrO2 详情 详情
(IX) 36444 1-(3,4-dimethoxyphenethyl)-2,4,6(1H,3H,5H)-pyrimidinetrione C14H16N2O5 详情 详情
(C) 28804 2,4,6-trimethylaniline 88-05-1 C9H13N 详情 详情
Extended Information