Trifluoroacetic acid → HCID 178448159、化合物

HRID 539062ノート

反応式

HRID 539062 の反応式
[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

参加物

4

反応物 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

生成物 1

HCID 178448159HCID 178448159、化合物収率 62%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-0efd72eca3904908ab4726d1ede632d1
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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