Cesium carbonate → 3-[2,5-Difluoro-4-(methylsulfonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20553

반응식

HRID 20553 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:27])[CH2:25][OH:26])[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12].[F:28][C:29]1[CH:34]=[C:33]([S:35]([CH3:38])(=[O:37])=[O:36])[C:32]([F:39])=[CH:31][C:30]=1F>C(#N)C>[F:28][C:29]1[CH:34]=[C:33]([S:35]([CH3:38])(=[O:37])=[O:36])[C:32]([F:39])=[CH:31][C:30]=1[O:7][C:8]1[CH:9]=[C:10]([CH:20]=[C:21]([O:23][C@@H:24]([CH3:27])[CH2:25][OH:26])[CH:22]=1)[C:11]([NH:13][C:14]1[CH:18]=[CH:17][N:16]([CH3:19])[N:15]=1)=[O:12]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzeneHCID 593468923-Hydroxy-5-{[(S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide

생성물 1

HCID 115402683-[2,5-Difluoro-4-(methylsulfonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide수율 1.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
160 °C

실험 절차

Caesium carbonate (523 mg) was added to a solution of 3-hydroxy-5-{[(1S)-2-hydroxy-1-methylethyl]oxy}-N-(1-methyl-1H-pyrazol-3-yl)benzamide (234 mg) and 1,2,4-trifluoro-5-(methylsulfonyl)benzene (169 mg) in acetonitrile (5 mL) was added. The mixture was heated in a sealed microwave vial to 160° C. for 7000 seconds and left to cool before being filtered and washed with acetonitrile (10 mL). The filtrate was evaporated in vacuo and chromatographed on silica, eluting with 0 to 10% methanol in ethyl acetate. This gave incomplete resolution so the mixture was purified by preparatory HPLC using a gradient of 5 to 95% acetonitrile in water to afford the desired compound (5.1 mg)

후처리

  1. additionwas added
  2. waitleft
  3. temperatureto cool
  4. filtrationbefore being filtered
  5. washwashed with acetonitrile (10 mL)
  6. customThe filtrate was evaporated in vacuo
  7. customchromatographed on silica
  8. washeluting with 0 to 10% methanol in ethyl acetate
  9. customThis gave incomplete resolution so the mixture was purified by preparatory HPLC

출처 및 근거

ORD 기록
ord-f5db6578902c40369809c04aab9c4f72
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745475B2

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