Hydrochloric Acid → 7-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid

HRID 1293711Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][C:12]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:11][C:10]=12)=[O:5])C.O[Li].O.Cl>C1COCC1.CO.O>[F:18][C:15]([F:16])([F:17])[C:14]1[N:9]2[N:8]=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[C:10]2[CH:11]=[C:12]([C:19]2[CH:20]=[CH:21][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:23][CH:24]=2)[CH:13]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (example C.22 step 7) (1.21 g, 3.0 mmol) in THF (15 mL), MeOH (1.8 mL) and H2O (4.8 mL) was added LiOH.H2O (0.3.8 g, 9.0 mmol) and the reaction mixture was stirred at 23° C. for 18 h. Poured into ice water, adjusted with 1 N HCl to pH 2–3, filtered the precipitate off, washed with H2O and dried at HV to give the title compound as an off-white solid (1.08 g, 96%). MS (ISN) 373 [(M−H)−]; mp>250° C.

Workup

filtrationfiltered the precipitate off,
washwashed with H2O
customdried at HV

Sources & evidence

ORD record: ord-a8ab87aa4f8840bd87805091fcea8260
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238808B2

Reaction notes

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