Cesium carbonate → HCID 21948801, compound

HRID 2215381Notes

Reaction equation

HRID 2215381 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:28])([CH3:27])[CH2:11][C:12](=[O:26])[C:13]([NH:15][C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH:18]=[CH:19][CH:20]=[N:21]4)=[O:14])[C:4]=2[O:3][CH2:2]1.[F:29][C:30]([Si](C)(C)C)([F:32])[F:31].C(=O)([O-])[O-].[Cs+].[Cs+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([CH3:28])([CH3:27])[CH2:11][C:12]([OH:26])([C:30]([F:32])([F:31])[F:29])[C:13]([NH:15][C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH:18]=[CH:19][CH:20]=[N:21]4)=[O:14])[C:4]=2[O:3][CH2:2]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 21948934HCID 21948934, compound

Product 1

HCID 21948801HCID 21948801, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

22 mg of 4-(1,3-benzodioxol-4-yl)-N-(quinolin-5-yl)-4-methyl-2-oxopentanamide and 0.04 ml of trifluoromethyltrimethylsilane in 1 ml of DMF are mixed at 0° C. with 11 mg of cesium carbonate. After 2 hours, a spatula-tip full of tetrabutylammonium fluoride is added, and after another 20 minutes, the reaction is added to water. It is extracted 3 times with ethyl acetate, washed with water and brine, dried, and the solvent is removed in a vacuum. The remaining oil is separated by chromatography on silica gel. 11 mg of 4-(1,3-benzodioxol-4-yl)-N-(quinolin-5-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanamide is obtained as a solid. Flash point: 164–167° C.

Workup

  1. waitafter another 20 minutes
  2. extractionIt is extracted 3 times with ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. customthe solvent is removed in a vacuum
  6. customThe remaining oil is separated by chromatography on silica gel

Sources & evidence

ORD record
ord-e6a9e1e232374e8c85fecb3a48da21de
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

Loading…