Hydrochloric Acid → HCID 56644527, 화합물

HRID 508404

반응식

HRID 508404 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 56644527HCID 56644527, 화합물수율 56.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0d6188b512ea48448d6dfeff5f43094f
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096500B2

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