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Water → 2-(4-(8-Chloro-2-oxo-3-(m-tolylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

HRID 476181
ノート
印刷プレビュー

反応式

HRID 476181 の反応式
[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.[CH3:34][C:35]1[CH:36]=[C:37]([S:41](Cl)(=[O:43])=[O:42])[CH:38]=[CH:39][CH:40]=1.O>ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([S:41]([C:37]4[CH:36]=[C:35]([CH3:34])[CH:40]=[CH:39][CH:38]=4)(=[O:43])=[O:42])[C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:25])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 27345953-Methylbenzenesulphonyl chlorideHCID 668963372-(4-(8-chloro-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile2 回

生成物 1

HCID 498551412-(4-(8-Chloro-2-oxo-3-(m-tolylsulfonyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒

実験手順

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 3-methylbenzene-1-sulfonyl chloride (40 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: 29 mg (40%); 1H NMR (CDCl3, 300 MHz): δ 9.605 (s, 1H), 8.023-8.093 (m, 3H), 7.72-7.748 (dd, 2H, J=6.6 Hz, 1.8 Hz), 7.44-7.551 (m, 5H), 6.855-6.862 (d, 1H, J=2.1 Hz), 2.44 (s, 3H), 1.82 (s, 6H); MS: m/z 517 (M+).

後処理

  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)

出典と根拠

ORDレコード
ord-851d5ced26904bcbb56680d787a2eb41
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637670B2

反応ノート

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