Water → HCID 89962890, 화합물

HRID 337907

반응식

HRID 337907 반응식
[F:1][C:2]1[CH:7]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)[CH:5]=[C:4]([F:20])[C:3]=1[S:21]([NH2:24])(=[O:23])=[O:22].[F:25][C:26]1[N:31]=[C:30](F)[CH:29]=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:20][C:4]1[CH:5]=[C:6]([O:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)[CH:7]=[C:2]([F:1])[C:3]=1[S:21]([NH:24][C:28]1[CH:29]=[CH:30][N:31]=[C:26]([F:25])[N:27]=1)(=[O:23])=[O:22]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1377162,4-DifluoropyrimidineHCID 89962731HCID 89962731, 화합물

생성물 1

HCID 89962890HCID 89962890, 화합물수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of the 2,6-difluoro-4-{[(1S*,2R*)-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}benzenesulfonamide (0.23 g, 0.65 mmol) prepared in Example 111c, 2,4-difluoropyrimidine (0.23 g, 1.96 mmol) and potassium carbonate (0.36 g, 2.61 mmol) in DMF (6.5 mL) was stirred at 120° C. for 3 hours. After allowing to cool, water (50 mL) was added to the reaction solution, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was washed twice with water (50 mL) and dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (ethyl acetate/methanol=6:1) to yield the title compound (150 mg, 51%) as a colorless amorphous solid.

후처리

  1. temperatureto cool
  2. extractionfollowed by extraction with ethyl acetate (50 mL)
  3. washThe thus obtained organic layer was washed twice with water (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with silica gel chromatography (ethyl acetate/methanol=6:1)

출처 및 근거

ORD 기록
ord-dfd2049633c94755aa00dccbf896d9a1
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889741B2

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