Cyclopropylmethoxide → 6-(4-Chloro-phenyl)-5-cyclopropylmethoxy-3-trifluoromethyl-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide

HRID 416475Notes

Reaction equation

HRID 416475 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.[CH:29]1([CH2:32][O-:33])[CH2:31][CH2:30]1>CS(C)=O>[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:33][CH2:32][CH:29]3[CH2:31][CH2:30]3)=[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

4

Reactant 2

HCID 21253811CyclopropylmethoxideHCID 866347045-Bromo-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide

Product 1

HCID 444634646-(4-Chloro-phenyl)-5-cyclopropylmethoxy-3-trifluoromethyl-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 0.048 g 5-bromo-6-(4-chloro-phenyl)-3-trifluoromethyl-pyrazine-2-carboxylic acid (2-cyclopropyl-2-hydroxy-propyl)-amide in 0.3 ml dimethylsulfoxide was added 0.2 ml of a 1M solution of cyclopropylmethoxide in dimethylsulfoxide and the mixture was stirred at room temperature for 30 min. The orange reaction mixture was partitioned between 10% citric acid and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel with heptane: ethyl acetate=9:1 to 1:1 to yield 0.015 g of the title compound as white solid. MS (M+H) at 468.3.

Workup

  1. customThe orange reaction mixture was partitioned between 10% citric acid 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-f5d6a305bc024684abb1a14d53170b8f
Source dataset
uspto-grants-2012_01
Patent number
US08088920B2

Reaction notes

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