2-chloro-2-(3,4-dimethoxyphenyl)acetonitrile -Drug Synthesis Database

【结构式】

【分子编号】25855

【品名】2-chloro-2-(3,4-dimethoxyphenyl)acetonitrile

【CA登记号】7537-07-7

【分子式】C₁₀H₁₀ClNO₂

【分子量】211.64764

【元素组成】C 56.75% H 4.76% Cl 16.75% N 6.62% O 15.12%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

Condensation of 2-chloro-2-(3,4-dimethoxyphenyl)acetonitrile (I) with p-thiocresol (II) in the presence of K2CO3 gave thioether (III). Alternatively, thioether (III) was obtained by reaction of the anion of (3,4-dimethoxyphenyl)acetonitrile (IV) with p-tolyl disulfide (V). Subsequent alkylation of (III) with 1-bromo-5-chloropentane using NaH in DMSO produced the 5-chloropentyl derivative (VI). This was finally condensed with tetrahydroisoquinoline (VII) to yield the title compound.

参考文献中间体

合成目标

【1】 Berger, D.; et al.; Novel multidrug resistance reversal agents. J Med Chem 1999, 42, 12, 2145.

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)	25855	2-chloro-2-(3,4-dimethoxyphenyl)acetonitrile	7537-07-7	C₁₀H₁₀ClNO₂	详情	详情
(III)	25856	2-(3,4-dimethoxyphenyl)-2-[(4-methylphenyl)sulfanyl]acetonitrile		C₁₇H₁₇NO₂S	详情	详情
(IV)	25857	2-(3,4-dimethoxyphenyl)acetonitrile	93-17-4	C₁₀H₁₁NO₂	详情	详情
(VI)	25858	7-chloro-2-(3,4-dimethoxyphenyl)-2-[(4-methylphenyl)sulfanyl]heptanenitrile		C₂₂H₂₆ClNO₂S	详情	详情
(VII)	25859	6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; 6-methoxy-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether		C₁₁H₁₅NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Condensation of alpha-chloro-(3,4-dimethoxyphenyl)acetonitrile (I) with p-thiocresol (II) in the presence of K2CO3 gave thioether (III). Alternatively, thioether (III) was obtained by reaction of the anion of (3,4-dimethoxyphenyl)acetonitrile (IV) with p-tolyl disulfide (V). Subsequent alkylation of (III) with 1-bromo-5-chloropentane using NaH in DMSO produced the 5-chloropentyl derivative (VI). This was then condensed with tetrahydroisoquinoline (VII) to yield the tertiary amine (VIII). Alkylation of the phenolic hydroxyl group of (VIII) with 2-chloroethyl tosylate produced the 2-chloroethyl ether (IX). Finally, reactionof (IX) with imidazole (X) and NaH in DMF furnished the title compound.

参考文献中间体

合成目标

【1】 Berger, D.; et al.; Novel multidrug resistance reversal agents. J Med Chem 1999, 42, 12, 2145.

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)	25855	2-chloro-2-(3,4-dimethoxyphenyl)acetonitrile	7537-07-7	C₁₀H₁₀ClNO₂	详情	详情
(III)	25856	2-(3,4-dimethoxyphenyl)-2-[(4-methylphenyl)sulfanyl]acetonitrile		C₁₇H₁₇NO₂S	详情	详情
(IV)	25857	2-(3,4-dimethoxyphenyl)acetonitrile	93-17-4	C₁₀H₁₁NO₂	详情	详情
(VI)	25858	7-chloro-2-(3,4-dimethoxyphenyl)-2-[(4-methylphenyl)sulfanyl]heptanenitrile		C₂₂H₂₆ClNO₂S	详情	详情
(VII)	25860	7-methoxy-1,2,3,4-tetrahydro-6-isoquinolinol		C₁₀H₁₃NO₂	详情	详情
(VIII)	25861	2-(3,4-dimethoxyphenyl)-7-[6-hydroxy-7-methoxy-3,4-dihydro-2(1H)-isoquinolinyl]-2-[(4-methylphenyl)sulfanyl]heptanenitrile		C₃₂H₃₈N₂O₄S	详情	详情
(IX)	25862	7-[6-(2-chloroethoxy)-7-methoxy-3,4-dihydro-2(1H)-isoquinolinyl]-2-(3,4-dimethoxyphenyl)-2-[(4-methylphenyl)sulfanyl]heptanenitrile		C₃₄H₄₁ClN₂O₄S	详情	详情
(X)	10255	Imidazole; 1H-Imidazole	288-32-4	C₃H₄N₂	详情	详情

Extended Information