Hydrochloric Acid → 2-Cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-5-methylpyrazolo[1,5-a]pyridine-3-carboxylic Acid
Reaction equation
[CH:1]1([C:4]2[C:23]([C:24]([O:26]C)=[O:25])=[C:7]3[CH:8]=[C:9]([CH3:22])[CH:10]=[C:11]([O:12][CH2:13][C:14]4[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=4[F:21])[N:6]3[N:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCOCC1>[CH:1]1([C:4]2[C:23]([C:24]([OH:26])=[O:25])=[C:7]3[CH:8]=[C:9]([CH3:22])[CH:10]=[C:11]([O:12][CH2:13][C:14]4[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=4[F:21])[N:6]3[N:5]=2)[CH2:3][CH2:2]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A solution of 384 mg (1.02 mmol) of methyl 2-cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-5-methylpyrazolo[1,5-a]pyridine-3-carboxylate from Example 99A in 10.6 ml of dioxane was admixed with 10.2 ml (10.2 mmol) of 1 N sodium hydroxide solution and the mixture was stirred at 100° C. for 7 h. The reaction solution was cooled and adjusted to pH 2 with 1 N hydrochloric acid. The solids that precipitated out were filtered off and dried under high vacuum. The filtrate was admixed once again with 1 N hydrochloric acid. The solids that precipitated out were filtered off and dried under high vacuum together with the previously isolated solids. A total of 361 mg of the title compound (74% by LC-MS, 73% of theory) were obtained and were converted without further purification.
Workup
- temperatureThe reaction solution was cooled
- customThe solids that precipitated out
- filtrationwere filtered off
- customdried under high vacuum
- customThe solids that precipitated out
- filtrationwere filtered off
- customdried under high vacuum together with the previously isolated solids
Sources & evidence
- ORD record
- ord-c3f445d7fa774bd0ac08e418de1d41eb
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422285B2
Reaction notes
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