Acetonitrile → 7-(Cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic Acid

HRID 1486287Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 220 mg (0.469 mmol, 71% pure) of 7-(cyclohexylmethoxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester from Example 119A 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 drawn off under reduced pressure and acetonitrile (5 ml) was added to the residue, and then trifluoroacetic acid (2 ml) was added dropwise. The resulting precipitate was filtered off and dried under reduced pressure, which gave 110 mg (74% of theory, 95% pure) of the target compound.

Workup

additionwas added to the residue
filtrationThe resulting precipitate was filtered off
customdried under reduced pressure, which
customgave 110 mg (74% of theory, 95% pure) of the target compound

Sources & evidence

ORD record: ord-dc3355e5b7a8427baa51c021caa0c969
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422285B2

Reaction notes

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