Trifluoroacetic acid → HCID 178519144、化合物

HRID 539131ノート

反応式

HRID 539131 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][CH:38]=[CH:37][N:36]=5)[CH2:33][O:32][C:31]4=[O:41])=[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>CC#N.CO.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][CH:38]=[CH:37][N:36]=5)[CH2:33][O:32][C:31]4=[O:41])=[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

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 68089128(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-(pyridin-2-yl)oxazolidin-2-one

生成物 1

HCID 178519144HCID 178519144、化合物収率 77.1%

試薬・触媒・溶媒 1

HCID 21864137Acetonitrile methanol water溶媒

実験手順

To (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-(pyridin-2-yl)oxazolidin-2-one (0.090 g, 0.16 mmol) was added TFA (10 mL) and the reaction was stirred at ambient temperature for 2 hours. The reaction was concentrated in vacuo and the resulting material dissolved in MeOH/CH3CN/water (1:1:1, 30 mL total) and stirred for 20 minutes at ambient temperature. The mixture was basified by adding NaHCO3 (saturated aqueous solution) and the solid that formed was isolated by filtration. The solids were slurried in CH3CN/MeOH/water (1:1:5, 40 mL total) and the material filtered and dried in vacuo to yield (S)-3-(3-(3-fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (0.054 g, 77.1%). LCMS (APCI+) m/z 443 [M+H]+.

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe resulting material dissolved in MeOH/CH3CN/water (1:1:1, 30 mL total)
  3. stirringstirred for 20 minutes at ambient temperature
  4. additionby adding NaHCO3 (saturated aqueous solution)
  5. customthe solid that formed
  6. customwas isolated by filtration
  7. filtrationthe material filtered
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-af080da5b2864b0b9cdb644c05df3d96
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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