Cesium carbonate → HCID 117843200, compound

HRID 2209064Notes

Reaction equation

HRID 2209064 reaction equation
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]

Participants

7

Reactant 3

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

Product 2

HCID 117843200HCID 117843200, compoundHCID 117843532HCID 117843532, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0f145a2b3c5a4aa5a31c7afbd8d3a659
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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