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Trifluoroacetic acid → HCID 178455828, 화합물

HRID 539066
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HRID 539066 반응식
[CH2:1]([C@H:3]1[CH2:7][O:6][C:5](=[O:8])[N:4]1[C:9]1[CH:14]=[CH:13][N:12]2[N:15]=[CH:16][C:17]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:28]=[CH:27][N:26](COCC[Si](C)(C)C)[N:25]=4)=[CH:20][CH:19]=3)=[C:11]2[N:10]=1)[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:26]1[CH:27]=[N:28][C:24]([C:21]2[CH:20]=[CH:19][C:18]([C:17]3[CH:16]=[N:15][N:12]4[CH:13]=[CH:14][C:9]([N:4]5[C@@H:3]([CH2:1][CH3:2])[CH2:7][O:6][C:5]5=[O:8])=[N:10][C:11]=34)=[CH:23][CH:22]=2)=[N:25]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 68088869(S)-4-ethyl-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 178455828HCID 178455828, 화합물수율 45.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of (S)-4-ethyl-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 (0.024 g, 0.047 mmol) in DCM (1 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 partitioned between EtOAc and aqueous satd. NaHCO3. The aqueous layer was further extracted with EtOAc. The combined organic extracts were washed with brine, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (1-5% 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-ethyloxazolidin-2-one (0.008 g, 45%) as a beige solid. MS (APCI+) m/z 376 [M+H]+.

후처리

  1. concentrationThe solvent was concentrated
  2. customthe residue partitioned between EtOAc and aqueous satd
  3. extractionThe aqueous layer was further extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. addition(phase separator silicone treated filter paper)
  7. concentrationconcentrated
  8. custompurified on silica gel (1-5% 7N ammonia in MeOH/dichloromethane)

출처 및 근거

ORD 기록
ord-7ec1a014f1414329869583b8259fbd9a
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865726B2

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