Cesium carbonate → 6-(4-Chloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-3-trifluoromethyl-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide

HRID 416474Notes

Reaction equation

[CH:1]1([C:4]([OH:28])([CH3:27])[CH2:5][NH:6][C:7]([C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[N:13][C:12](Br)=[C:11]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1.[C:29](=[O:32])([O-])[O-].[Cs+].[Cs+]>C(O)C(F)(F)F>[CH:1]1([C:4]([OH:28])([CH3:27])[CH2:5][NH:6][C:7]([C:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[N:13][C:12]([O:32][CH2:29][C:15]([F:18])([F:17])[F:16])=[C:11]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 0.050 g 5-bromo-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide and 0.050 g cesium carbonate in 0.5 ml trifluoroethanol was heated to 80° C. for 20 min. The reaction mixture was partitioned between 10% citric acid and ethyl acetate. The phases were separated and the organic phase was washed with brine evaporated and the crystalline residue was triturated under heptane to yield 0.040 g of the title compound as off white powder. MS (M−H) at 496.4 and 498.4.

Workup

customThe reaction mixture was partitioned between 10% citric acid and ethyl acetate
customThe phases were separated
washthe organic phase was washed with brine
customevaporated
customthe crystalline residue was triturated under heptane

Sources & evidence

ORD record: ord-4de699042ce245c8b9901268e55fe97e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088920B2

Reaction notes

Loading…