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Water → 2-(8-Chloro-1-(4-(2-cyanopropan-2-yl)phenyl)-2-oxo-1H-imidazo[4,5-c]quinolin-3(2H)-ylsulfonyl)benzonitrile

HRID 476182
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HRID 476182 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1.C(N(CC)CC)C.[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[S:42](Cl)(=[O:44])=[O:43])#[N:35].O>ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([S:42]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=4[C:34]#[N:35])(=[O:44])=[O:43])[C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([C:22]#[N:23])([CH3:24])[CH3:25])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 668963372-(4-(8-chloro-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile2회

생성물 1

HCID 498551422-(8-Chloro-1-(4-(2-cyanopropan-2-yl)phenyl)-2-oxo-1H-imidazo[4,5-c]quinolin-3(2H)-ylsulfonyl)benzonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(4-(8-chloro-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 2, 50 mg, 0.14 mmol) and triethylamine (28 mg, 0.28 mmol) in dichloromethane (6 ml) was added 2-cyanobenzene-1-sulfonyl chloride (42 mg, 0.21 mmol) at 0° C. The reaction was stirred at RT for 3 hours. The reaction mixture was poured into cold water and organic layer was separated. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine dried over sodium sulfate and evaporated to dryness. The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain the title compound. Yield: 24 mg (33%); 1H NMR (CDCl3, 300 MHz): δ 9.698 (s, 1H), 8.496-8.525 (d, 1H, 8.7 Hz), 8.093-8.123 (d, 1H, J=9 Hz), 7.823-7.920 (m, 3H), 7.71-7.739(d, 2H, J=8.7 Hz), 7.525-7.563 (dd, 1H, J=9.3, 2.1 Hz), 7.46-7.488(d, 2H, J=8.4 Hz), 6.863-6.870 (d, 1H, 2.1 Hz), 1.798 (s, 6H); MS: m/z 528 (M+).

후처리

  1. customwas separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe crude product was purified by column chromatography (silica gel, 2% acetone in chloroform)

출처 및 근거

ORD 기록
ord-8e3a661be52e4976b17acf4c0895af09
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08637670B2

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