Water → HCID 66682285, 화합물

HRID 1964594노트

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HRID 1964594 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:14]2[N:15](C(OC(C)(C)C)=O)[C:16]([C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[CH:17][CH:18]=2)[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=1.[F:31][C:32]1[CH:33]=[C:34]([S:39]([NH:42][CH3:43])(=[O:41])=[O:40])[CH:35]=[CH:36][C:37]=1F.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:31][C:32]1[CH:33]=[C:34]([S:39]([NH:42][CH3:43])(=[O:40])=[O:41])[CH:35]=[CH:36][C:37]=1[O:1][C:2]1[CH:3]=[C:4]([C:14]2[NH:15][C:16]([C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[CH:17][CH:18]=2)[CH:5]=[C:6]([O:8][C@@H:9]([CH3:13])[CH2:10][O:11][CH3:12])[CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 84679853,4-difluoro-N-methylbenzene-1-sulfonamideHCID 66681373t-Butyl 2-{3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate

생성물 1

HCID 66682285HCID 66682285, 화합물수율 30%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

t-Butyl 2-{3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate (60.0 mg, 0.139 mmol) synthesized in Example (38d) and 3,4-difluoro-N-methylbenzenesulfonamide (47.4 mg, 0.229 mmol) synthesized in Example (58a) were dissolved in N,N-dimethylformamide (5.0 mL), and potassium carbonate (77.0 mg, 0.557 mmol) was added, followed by stirring at 100° C. for 19 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, water (20 mL) was added, and extraction was carried out with ethyl acetate (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-25%) to afford the desired compound (21.1 mg, yield 30%) as a white solid.

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialsubsequently dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified
  7. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-25%)

출처 및 근거

ORD 기록
ord-0bc8adecefa3436d944e7485e78b9d4c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415359B2

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