2,2,2-Trifluoroethanol → HCID 24800611, compound

HRID 1929864Notes

Reaction equation

HRID 1929864 reaction equation
[CH:1]1([C@:4]([OH:24])([CH3:23])[CH2:5][NH:6][C:7]([C:9]2[CH:14]=[N:13][C:12](Br)=[C:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C.[F:37][C:38]([F:42])([F:41])[CH2:39][OH:40]>>[CH:1]1([C@:4]([OH:24])([CH3:23])[CH2:5][NH:6][C:7]([C:9]2[CH:14]=[N:13][C:12]([O:40][CH2:39][C:38]([F:42])([F:41])[F:37])=[C:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 86616978HCID 86616978, compound

Product 1

HCID 24800611HCID 24800611, compoundYield 98%

Procedure

To a solution of 0.041 g (0.001 mol) 5-bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid ((R)-2-cyclopropyl-2-hydroxy-propyl)-amide (example 62 a) in 1.0 ml 2,2,2-trifluoroethanol was added 0.200 g (0.006 mol) cesium carbonate and the mixture was stirred at room temperature for 7 days. The reaction mixture was partitioned between water and ethyl acetate, the phases were separated and the organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=2:1 to yield 0.042 g (98% yield) of the title compound as white crystals melting at 96-97° C.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe phases were separated
  3. customthe organic phase was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-79ab9e36aba94832ace87bb097446cff
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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