Ammonia → HCID 86686376, 화합물

HRID 1043945노트

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HRID 1043945 반응식
C1N=C[N:3](C(N2C=NC=C2)=O)C=1.[F:13][C:14]1[CH:19]=[C:18]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([O:27][CH3:28])[C:21]=2[CH3:29])[CH:17]=[CH:16][C:15]=1[C:30]1[N:34]([C@H:35]2[CH2:39][CH2:38][O:37][CH2:36]2)[N:33]=[CH:32][C:31]=1[C:40]([OH:42])=O.N>CN(C=O)C>[F:13][C:14]1[CH:19]=[C:18]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([O:27][CH3:28])[C:21]=2[CH3:29])[CH:17]=[CH:16][C:15]=1[C:30]1[N:34]([C@H:35]2[CH2:39][CH2:38][O:37][CH2:36]2)[N:33]=[CH:32][C:31]=1[C:40]([NH2:3])=[O:42]

참가 물질

5

반응물 3

HCID 222Ammonia2회HCID 682631,1'-CarbonyldiimidazoleHCID 866863755-[2-fluoro-4-(2-methoxy-3,5-dimethylpyridin-4-yl)phenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylic acid

생성물 1

HCID 86686376HCID 86686376, 화합물수율 96.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

CDI (21.4 g) was added at one time to a solution of 5-[2-fluoro-4-(2-methoxy-3,5-dimethylpyridin-4-yl)phenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylic acid (38.7 g) in DMF (290 mL) at room temperature, and the mixture was stirred at room temperature for 95 minutes. 28% aqueous ammonia (95 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 35 minutes. 28% aqueous ammonia (95 mL) was added again to the reaction mixture, and the mixture was stirred at room temperature for 90 minutes. The reaction mixture was concentrated under reduced pressure. Chloroform (250 mL) and water (80 mL) were added to the resulting residue, and the organic layer was separated. The aqueous layer was re-extracted with chloroform (50 mL). The combined organic layers were sequentially washed with a saturated aqueous ammonium chloride solution (60 mL×3) and brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was passed through a silica pad (NH-silica gel). The filtrate was concentrated under reduced pressure to give the title compound (37.2 g).

후처리

  1. stirringthe mixture was stirred at room temperature for 35 minutes
  2. stirringthe mixture was stirred at room temperature for 90 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionChloroform (250 mL) and water (80 mL) were added to the resulting residue
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was re-extracted with chloroform (50 mL)
  7. washThe combined organic layers were sequentially washed with a saturated aqueous ammonium chloride solution (60 mL×3) and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-50bbe1a53a894e27b8e071e1a1a98b2a
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563565B2

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