HCID 67034134、化合物 → HCID 178519150、化合物

HRID 539101ノート

反応式

HRID 539101 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][C:27]([N:30]4[C@@H:34]([C:35]5[CH:40]=[CH:39][C:38]([F:41])=[CH:37][N:36]=5)[CH2:33][O:32][C:31]4=[O:42])=[N:26][C:25]=23)[CH:5]=[CH:6][C:7]=1[C:8]1[N:12]=[CH:11][N:10](COCC[Si](C)(C)C)[N:9]=1>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][C:27]([N:30]4[C@@H:34]([C:35]5[CH:40]=[CH:39][C:38]([F:41])=[CH:37][N:36]=5)[CH2:33][O:32][C:31]4=[O:42])=[N:26][C:25]=23)[CH:5]=[CH:6][C:7]=1[C:8]1[N:12]=[CH:11][NH:10][N:9]=1

参加物

3

反応物 1

HCID 67034134HCID 67034134、化合物

生成物 1

HCID 178519150HCID 178519150、化合物収率 75.5%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

To the solid (S)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (5.8 g, 9.8 mmol) was added TFA (40 mL) and the reaction stirred at ambient temperature for 2 hours. The reaction was concentrated in vacuo and the residue was dissolved in acetonitrile/methanol (1:1, 70 mL). Water (30 mL) was added and the mixture was stirred at ambient temperature for 3 hours. The aqueous layer was made basic with NaHCO3 (saturated solution) and the organic layer was removed in vacuo. The solid that formed was filtered and dried in vacuo. The solid was taken up in acetone (100 mL) and water added (500 mL) slowly. After complete addition, the slurry was stirred for 1 hour at ambient temperature. The slurry was filtered and the solid dried in vacuo for 36 hours to yield (S)-3-(3-(3-fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (3.4 g, 7.4 mmol, 75% yield). LCMS (APCI+) m/z 461 [M+H]+.

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in acetonitrile/methanol (1:1, 70 mL)
  3. additionWater (30 mL) was added
  4. stirringthe mixture was stirred at ambient temperature for 3 hours
  5. customthe organic layer was removed in vacuo
  6. customThe solid that formed
  7. filtrationwas filtered
  8. customdried in vacuo
  9. additionwater added (500 mL) slowly
  10. additionAfter complete addition
  11. stirringthe slurry was stirred for 1 hour at ambient temperature
  12. filtrationThe slurry was filtered
  13. customthe solid dried in vacuo for 36 hours

出典と根拠

ORDレコード
ord-c9522d7796024b438f3477481828a300
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

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