Sodium Hydroxide → 7-Benzyloxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

HRID 1486305Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 390 mg (1.13 mmol) of 7-benzyloxy-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (Example 7A) in 6 ml of 1,4-dioxane was admixed with 4 ml of 2 M sodium hydroxide solution. The mixture was stirred at 100° C. for a further 18 hours. The reaction mixture was cooled under reduced pressure and then concentrated under reduced pressure. The residue was admixed with acetonitrile (10 ml) and water (2 ml), followed by 2 ml of trifluoroacetic acid, which was added dropwise. The resulting precipitate was filtered off and dried under reduced pressure, which gave 262 mg (72% yield, 92% pure) of the target compound.

Workup

temperatureThe reaction mixture was cooled under reduced pressure
concentrationconcentrated under reduced pressure
additionwas added dropwise
filtrationThe resulting precipitate was filtered off
customdried under reduced pressure, which
customgave 262 mg (72% yield, 92% pure) of the target compound

Sources & evidence

ORD record: ord-b9bad5c557f24de7929fe575e62fe082
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422285B2

Reaction notes

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