Trifluoroacetic acid → HCID 178448159, 화합물

HRID 539062노트

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HRID 539062 반응식
[CH2:1]([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:29]=[CH:28][N:27](COCC[Si](C)(C)C)[N:26]=4)=[CH:21][CH:20]=3)=[C:12]2[N:11]=1)[CH2:2][CH3:3].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:27]1[CH:28]=[N:29][C:25]([C:22]2[CH:21]=[CH:20][C:19]([C:18]3[CH:17]=[N:16][N:13]4[CH:14]=[CH:15][C:10]([N:5]5[C@@H:4]([CH2:1][CH2:2][CH3:3])[CH2:8][O:7][C:6]5=[O:9])=[N:11][C:12]=34)=[CH:24][CH:23]=2)=[N:26]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 67035120(S)-4-propyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one

생성물 1

HCID 178448159HCID 178448159, 화합물수율 62%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of (S)-4-propyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.039 g, 0.075 mmol) in DCM (0.4 mL) was treated with trifluoroacetic acid (0.4 mL) at ambient temperature. The mixture was stirred for 18 hours. The solvent was concentrated and the residue was partitioned between EtOAc and aqueous saturated NaHCO3. The aqueous layer was further extracted with EtOAc. The combined organic extracts were washed with brine, dried, concentrated and purified by column chromatography (1-5% 20% 7N ammonia in MeOH/dichloromethane) to give (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one (0.018 g, 62%) as a beige solid. LCMS (APCI+) m/z 390 [M+H]+.

후처리

  1. concentrationThe solvent was concentrated
  2. customthe residue was partitioned between EtOAc and aqueous saturated NaHCO3
  3. extractionThe aqueous layer was further extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by column chromatography (1-5% 20% 7N ammonia in MeOH/dichloromethane)

출처 및 근거

ORD 기록
ord-0efd72eca3904908ab4726d1ede632d1
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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