Trifluoroacetic acid → HCID 178519144, 화합물

HRID 539131노트

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HRID 539131 반응식
[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

참가 물질

4

반응물 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

생성물 1

HCID 178519144HCID 178519144, 화합물수율 77.1%

시약·촉매·용매 1

HCID 21864137Acetonitrile methanol water용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-af080da5b2864b0b9cdb644c05df3d96
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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