Cesium carbonate → HCID 117843200、化合物

HRID 2209064ノート

反応式

HRID 2209064 の反応式
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]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 178488441HCID 178488441、化合物

生成物 2

HCID 117843200HCID 117843200、化合物HCID 117843532HCID 117843532、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0f145a2b3c5a4aa5a31c7afbd8d3a659
出典データセット
uspto-grants-2016_06
特許番号
US09376441B2

反応ノート

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