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Trifluoroacetic acid → (S)-3-(3-(4-(1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one

HRID 538980
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HRID 538980 반응식
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[N:26](COCC[Si](C)(C)C)[CH:27]=[CH:28][N:29]=4)=[CH:21][CH:20]=3)=[C:12]2[N:11]=1)([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[NH:26]1[CH:27]=[CH:28][N:29]=[C:25]1[C:22]1[CH:23]=[CH:24][C:19]([C:18]2[CH:17]=[N:16][N:13]3[CH:14]=[CH:15][C:10]([N:5]4[C@@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:8][O:7][C:6]4=[O:9])=[N:11][C:12]=23)=[CH:20][CH:21]=1
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67034475(S)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one

생성물 1

HCID 50997719(S)-3-(3-(4-(1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one수율 61.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-4-isopropyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (2.09 g, 4.03 mmol) was dissolved in dichloromethane (20 mL) and trifluoroacetic acid (25 mL) was added and the mixture allowed to stir at ambient temperature for 12 hours. The reaction mixture was concentrated and the residue partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (100 mL). The aqueous layer was washed with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to give a light yellow solid. Purification of the crude material by column chromatography, eluting with a gradient of 0-4% (9:1 MeOH/NH4OH)/EtOAc, provided (S)-3-(3-(4-(1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one as a yellow solid (961.3 mg, 61%). LCMS (APCI+) m/z 389 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 8.57 (d, J=7.8 Hz, 1H), 8.39 (s, 1H), 8.04 (d, J=8.6 Hz, 2H), 8.03 (d, J=7.8 Hz, 1H), 7.89 (d, J=8.6 Hz, 2H), 7.19 (s, 2H), 4.95-4.91 (m, 1H), 4.36-4.45 (m, 2H), 2.83-2.91 (m, 1H), 1.04 (d, J=7.0 Hz, 3H), 0.92 (d, J=7.0 Hz, 3H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between saturated aqueous NaHCO3 (50 mL) and EtOAc (100 mL)
  3. washThe aqueous layer was washed with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a light yellow solid
  9. customPurification of the crude material by column chromatography
  10. washeluting with a gradient of 0-4% (9:1 MeOH/NH4OH)/EtOAc

출처 및 근거

ORD 기록
ord-7c57d8acebf641a395159f52228e7352
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865726B2

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