Hydrochloric Acid → 2-Cyclopropyl-5-methyl-7-[(2,3,6-trifluorobenzyl)oxy]pyrazolo[1,5-a]pyridine-3-carboxylic Acid

HRID 1486320Notes

Reaction equation

[CH:1]1([C:4]2[C:24]([C:25]([O:27]C)=[O:26])=[C:7]3[CH:8]=[C:9]([CH3:23])[CH:10]=[C:11]([O:12][CH2:13][C:14]4[C:19]([F:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=4[F:22])[N:6]3[N:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Cl>O1CCOCC1.CS(C)=O>[CH:1]1([C:4]2[C:24]([C:25]([OH:27])=[O:26])=[C:7]3[CH:8]=[C:9]([CH3:23])[CH:10]=[C:11]([O:12][CH2:13][C:14]4[C:19]([F:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=4[F:22])[N:6]3[N:5]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 462 mg (1.01 mmol; purity 85%) of methyl 2-cyclopropyl-5-methyl-7-[(2,3,6-trifluorobenzyl)oxy]pyrazolo[1,5-a]pyridine-3-carboxylate from Example 156A in 10.5 ml of dioxane and 3 ml of DMSO was admixed with 5.55 ml (11.10 mmol) of 2 N sodium hydroxide solution, and the mixture was stirred at 100° C. for 6.5 h. Another 1 ml (2 mmol) of 2 N sodium hydroxide solution was added and the mixture was stirred at 100° C. for a further 2.5 h. The reaction solution was cooled down to 0° C. and adjusted to pH 2 with 1 N hydrochloric acid. The solids that precipitated out were stirred for 30 min, filtered off and dried under high vacuum. 300 mg of the title compound were obtained (74% of theory, 93% purity) and were converted without further purification.

Workup

stirringthe mixture was stirred at 100° C. for a further 2.5 h
temperatureThe reaction solution was cooled down to 0° C.
customThe solids that precipitated out
stirringwere stirred for 30 min
filtrationfiltered off
customdried under high vacuum

Sources & evidence

ORD record: ord-f8690c72d72146d68c41455442735d5e
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422285B2

Reaction notes

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