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Methyl vinyl sulfone → 4-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline

HRID 547320
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HRID 547320 반응식
[H-].[Na+].[Cl:3][C:4]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1.[CH:22]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH2:23]>O1CCCC1>[Cl:3][C:4]1[C:13]2[N:14]=[CH:15][N:16]([CH2:17][C:18]([CH3:21])([O:20][CH2:23][CH2:22][S:24]([CH3:27])(=[O:26])=[O:25])[CH3:19])[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]=1
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참가 물질

5

반응물 3

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 98384584-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

생성물 1

HCID 866134654-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (60% dispersion in mineral oil, 58 mg, 1.45 mmol) was added to a stirred solution of 1-(4-chloro-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (described in U.S. Pat. No. 4,689,338 Example 189, Part D, 4.00 g, 14.5 mmol) in tetrahydrofuran (58 mL). After 5 minutes, methyl vinyl sulfone (3.10 g, 29.0 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 17 hours. The volatiles were removed under reduced pressure and the resulting oil was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane) to yield 4.3 g of 4-chloro-1-{2-methyl-2-[2-(methylsulfonyl)ethoxy]propyl}-1H-imidazo[4,5-c]quinoline as a foam.

후처리

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting oil was purified by flash chromatography (silica gel, eluted with 5% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-22ff6cc8f5214c0586b5d4477e90b99b
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07939526B2

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