Sodium Hydroxide → 2,5-Dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridine-3-carboxylic Acid

HRID 1486290Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 220 mg (0.469 mmol, 72% pure) of 2,5-dimethyl-7-(3-methylbutoxy)pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester from Example 122A in 4 ml of dioxane was admixed with 2 ml of 2 N sodium hydroxide solution. The resulting mixture was stirred at 100° C. for 15 h. The solvent was removed under reduced pressure. The residue was admixed with acetonitrile (5 ml), followed by the dropwise addition of trifluoroacetic acid (2 ml). The resulting precipitate was filtered off and dried under reduced pressure, which gave 45 mg (28% of theory, 90% pure) of the target compound.

Workup

customThe solvent was removed under reduced pressure
additionfollowed by the dropwise addition of trifluoroacetic acid (2 ml)
filtrationThe resulting precipitate was filtered off
customdried under reduced pressure, which
customgave 45 mg (28% of theory, 90% pure) of the target compound

Sources & evidence

ORD record: ord-cd409d39078f44b6a8a564f0ab83956a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422285B2

Reaction notes

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