Ammonia → HCID 86686376、化合物

HRID 1043945ノート

反応式

HRID 1043945 の反応式
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]

参加物

5

反応物 3

HCID 222Ammonia2 回HCID 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

生成物 1

HCID 86686376HCID 86686376、化合物収率 96.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-50bbe1a53a894e27b8e071e1a1a98b2a
出典データセット
uspto-grants-2013_10
特許番号
US08563565B2

反応ノート

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