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

HRID 269039Notes

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-86b068f29c9c4c95a9f3c25a0bacd4b1
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446113B2

Reaction notes

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