Sodium Chloride → 5-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid amide

Temperature

60 °C

To a solution of 5-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid (100 mg, 0.36 mmol) in DMF (8.3 mL) was added 1,1′-carbonyldiimidazole (60.6 mg, 0.36 mmol). The resulting reaction mixture was stirred for 1 h at 60° C. and then treated with an ammonium hydroxide solution (465 μL, 3.0 mmol) and stirred overnight at room temperature. The reaction mixture was then poured into aqueous sodium chloride (saturated) and the mixture was extracted with ethyl acetate. The combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution and then dried over sodium sulfate, filtered and evaporated. Concentration and purification by chromatography (silica, dichloromethane:methanol=99:1 to 95:5) afforded the title compound (79 mg, 79%) as a white solid. MS: m/e=331.2 [M+H]+.

1. customThe resulting reaction mixture
2. stirringstirred overnight at room temperature
3. extractionthe mixture was extracted with ethyl acetate
4. washThe combined organic layers were then washed with water and saturated sodium hydrogen carbonate solution
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated
8. concentrationConcentration and purification by chromatography (silica, dichloromethane:methanol=99:1 to 95:5)

ORD record

ord-56eef6e8504a40e9a1124dd828438597

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163728B2