Cesium carbonate → HCID 117843200, 화합물

HRID 2209064노트

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HRID 2209064 반응식
FC(F)(F)S(O[CH2:7][C:8]([F:11])([F:10])[F:9])(=O)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:24]2[N:29]=[C:28]([O:30][C@@H:31]([C@H:33]3[CH2:37][NH:36][C:35](=[O:38])[CH2:34]3)[CH3:32])[C:27]3[NH:39][CH:40]=[N:41][C:26]=3[CH:25]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:24]2[N:29]=[C:28]([O:30][C@@H:31]([C@H:33]3[CH2:37][NH:36][C:35](=[O:38])[CH2:34]3)[CH3:32])[C:27]3[N:39]([CH2:7][C:8]([F:11])([F:10])[F:9])[CH:40]=[N:41][C:26]=3[CH:25]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:24]2[N:29]=[C:28]([O:30][C@@H:31]([C@H:33]3[CH2:37][NH:36][C:35](=[O:38])[CH2:34]3)[CH3:32])[C:27]3[N:39]=[CH:40][N:41]([CH2:7][C:8]([F:11])([F:10])[F:9])[C:26]=3[CH:25]=2)[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178488441HCID 178488441, 화합물

생성물 2

HCID 117843200HCID 117843200, 화합물HCID 117843532HCID 117843532, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

2,2,2-trifluoroethyl trifluoromethanesulfonate (13 mg, 0.056 mmol) was added to a solution of (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.09 (20 mg, 0.052 mmol) and cesium carbonate (43 mg, 0.132 mmol) in 5 mL of DMF at room temperature. After 1 h, reaction mixture was taken up in ethyl acetate (100 mL) and washed with saturated NaHCO3 (aq) (2×100 mL) and brine. The separated organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to yield (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-3-(2,2,2-trifluoroethyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.10 and (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-1-(2,2,2-trifluoroethyl)-1H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)pyrrolidin-2-one 3.11.

후처리

  1. customreaction mixture
  2. washwashed with saturated NaHCO3 (aq) (2×100 mL) and brine
  3. dry with materialThe separated organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0f145a2b3c5a4aa5a31c7afbd8d3a659
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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