Hydrochloric Acid → HCID 56644527、化合物

HRID 508404

反応式

HRID 508404 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].Br[CH2:14][C:15]1[C:27]([F:28])=[CH:26][C:18]([C:19]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[O:20])=[C:17]([F:29])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:11])[F:9])[O:12][CH2:14][C:15]1[C:27]([F:28])=[CH:26][C:18]([C:19]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[O:20])=[C:17]([F:29])[CH:16]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 136091473-Chloro-4-(trifluoromethyl)phenolHCID 666671114-(Bromomethyl)-2,5-difluoro-N-(methylsulfonyl)benzamide

生成物 1

HCID 56644527HCID 56644527、化合物収率 56.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of 3-chloro-4-(trifluoromethyl)phenol (Preparation 5, 50 mg, 0.26 mmol), 4-(bromomethyl)-2,5-difluoro-N-(methylsulfonyl)benzamide (Preparation 4, 84 mg, 0.26 mmol) and potassium carbonate (71 mg, 0.51 mmol) in dimethyl sulfoxide (5 mL) was stirred at room temperature for 16 hours. A 2M aqueous solution of hydrogen chloride was added to the reaction mixture. The resulting precipitate was filtered, washed with diethyl ether (5 mL) and dried. The material was purified by reverse phase column chromatography (12 g C-18 biotage cartridge; eluents: MeCN+0.1% formic acid, and H2O+0.1% formic acid; Gradient: 30% MeCN, followed by gradient to 100% MeCN, 100% MeCN. Fractions containing product were combined and concentrated in vacuo to afford the title compound as a colourless solid (65 mg, 56%).

後処理

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with diethyl ether (5 mL)
  3. customdried
  4. customThe material was purified by reverse phase column chromatography (12 g C-18 biotage cartridge
  5. additionFractions containing product
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0d6188b512ea48448d6dfeff5f43094f
出典データセット
uspto-grants-2015_08
特許番号
US09096500B2

関連ノート

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