Hydrochloric Acid → HCID 58763948, compound

Temperature

40 °C

Acetic acid 3-[(2-chloroethyl)-(2,2-difluoropropyl)-carbamoyl]-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1-H-pyrazol-4-yl-ester I-6f (3.55 g, 6.69 mmol) was dissolved in 90 ml of methanol with warming in a 40° C. waterbath to give a clear colorless solution. The resulting solution was cooled to 0° C. (still a clear, colorless solution), followed by addition of K2CO3 (1.02 g, 7.31 mmol) in one portion as a solid (reaction mixture goes from colorless to yellow). Reaction stirred for 30 minutes at 0° C., followed by addition of concentrated hydrochloric acid (1.2 ml of 12.1 M, 14.5 mmol). Note: upon neutralization, reaction turns colorless and clear, then product begins to precipitate. The reaction was warmed to room temperature, then 45 ml of water was added, followed by stirring for 2.5 hours. The precipitated solids were collected by filtration and the resulting filtercake was washed with 50 ml of room temperature 2:1, methanol:water. Collected solids were dried at 50° C. and 10 mm for 1 hour to give 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-hydroxy-1H-pyrazole-3-carboxylic acid (2-chloroethyl)-(2,2-difluoropropyl)-amide I-6g (2.86 g, 87%) as a white solid.

1. customto give a clear colorless solution
2. temperatureThe resulting solution was cooled to 0° C. (still a clear, colorless solution),
3. customReaction
4. customupon neutralization, reaction
5. customto precipitate
6. temperatureThe reaction was warmed to room temperature
7. addition45 ml of water was added
8. stirringby stirring for 2.5 hours
9. filtrationThe precipitated solids were collected by filtration
10. washthe resulting filtercake was washed with 50 ml of room temperature 2:1, methanol
11. customCollected solids
12. customwere dried at 50° C.

ORD record

ord-3f7d5affb7a4420b8c4d0fc006ad7039

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07151097B2