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

HRID 1486282
Notes
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Reaction equation

HRID 1486282 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]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117859596Methyl 2-cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-5-methylpyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 1178596452-Cyclopropyl-7-[(2,6-difluorobenzyl)oxy]-5-methylpyrazolo[1,5-a]pyridine-3-carboxylic AcidYield 98.8%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

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

  1. temperatureThe reaction solution was cooled
  2. customThe solids that precipitated out
  3. filtrationwere filtered off
  4. customdried under high vacuum
  5. customThe solids that precipitated out
  6. filtrationwere filtered off
  7. customdried under high vacuum together with the previously isolated solids

Sources & evidence

ORD record
ord-c3f445d7fa774bd0ac08e418de1d41eb
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09422285B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes