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【结 构 式】

【分子编号】55709

【品名】2-chloro-4-methoxynicotinoyl chloride

【CA登记号】

【 分 子 式 】C7H5Cl2NO2

【 分 子 量 】206.02764

【元素组成】C 40.81% H 2.45% Cl 34.42% N 6.8% O 15.53%

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:(II)

The triarylcarbinol intermediate (IV) is obtained by two different ways: 1. The reaction of 2-chloro-4-methoxypyridine-3-carboxylic acid (I) with (COCl)2 in dichloromethane gives the acyl chloride (II), which is condensed with 2-methylsulfanylpyrimidin-4-yl lithium salt (III) in THF to yield the triarylcarbinol (IV). 2. The reaction of the lithium salt (III) with 0.4 equiv. of diethyl carbonate (V) in THF gives the symmetric ketone (VI), which is then condensed with the 2-chloro-4-methoxypyridin-3-yl lithium salt (VII) in THF to yield the desired triarylcarbinol intermediate (IV). The cyclization of the triarylcarbinol intermediate (IV) by means of Tes-H and TEA in 1,2-dichloroethane at 100 C gives the desired core structure (VIII), which is oxidized at its sulfanyl groups with MCPBA in chloroform to yield the sulfinyl derivative (IX). The reaction of (IX) with 4-methoxybenzylamine (X) at 85 ?C affords the protected diamine (XI). The demethylation of (XI) by means of EtS-Na in hot DMF provides the pyridinol (XII), which is finally N-deprotected by means of triflic acid to yield the target variolin B (1).

1 Morris, J.C.; Anderson, R.J.; Total synthesis of variolin B. Tetrahedron Lett 2001, 42, 49, 8697.
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) 55708 2-chloro-4-methoxynicotinic acid C7H6ClNO3 详情 详情
(II) 55709 2-chloro-4-methoxynicotinoyl chloride C7H5Cl2NO2 详情 详情
(III) 55710 [2-(methylsulfanyl)-4-pyrimidinyl]lithium C5H5LiN2S 详情 详情
(IV) 55711 (2-chloro-4-methoxy-3-pyridinyl){bis[2-(methylsulfanyl)-4-pyrimidinyl]}methanol C17H16ClN5O2S2 详情 详情
(V) 34197 dimethyl carbonate 616-38-6 C3H6O3 详情 详情
(VI) 55712 bis[2-(methylsulfanyl)-4-pyrimidinyl]methanone C11H10N4OS2 详情 详情
(VII) 55713 (2-chloro-4-methoxy-3-pyridinyl)lithium C6H5ClLiNO 详情 详情
(VIII) 55714 4-methoxy-9-(methylsulfanyl)-5-[2-(methylsulfanyl)-4-pyrimidinyl]pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine; methyl 9-(methylsulfanyl)-5-[2-(methylsulfanyl)-4-pyrimidinyl]pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-yl ether C17H15N5OS2 详情 详情
(IX) 55715 4-[4-methoxy-9-(methylsulfinyl)pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-5-yl]-2-pyrimidinyl methyl sulfoxide; 4-methoxy-9-(methylsulfinyl)-5-[2-(methylsulfinyl)-4-pyrimidinyl]pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine C17H15N5O3S2 详情 详情
(X) 15098 4-Methoxybenzylamine; (4-Methoxyphenyl)methanamine 2393-23-9 C8H11NO 详情 详情
(XI) 55716 N-(4-methoxybenzyl)-N-(4-{4-methoxy-9-[(4-methoxybenzyl)amino]pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-5-yl}-2-pyrimidinyl)amine; 4-methoxy-N-(4-methoxybenzyl)-5-{2-[(4-methoxybenzyl)amino]-4-pyrimidinyl}pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-9-amine C31H29N7O3 详情 详情
(XII) 55717 9-[(4-methoxybenzyl)amino]-5-{2-[(4-methoxybenzyl)amino]-4-pyrimidinyl}pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-4-ol C30H27N7O3 详情 详情
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