Sodium Hydroxide → HCID 117859583, compound

HRID 1486323Notes

Reaction equation

HRID 1486323 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:27])=[N:8][N:9]2[C:14]([O:15][CH2:16][C:17]3[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=3[F:24])=[CH:13][C:12]([O:25][CH3:26])=[CH:11][C:10]=12)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[F:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:17]=1[CH2:16][O:15][C:14]1[N:9]2[N:8]=[C:7]([CH3:27])[C:6]([C:4]([OH:5])=[O:3])=[C:10]2[CH:11]=[C:12]([O:25][CH3:26])[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117864562HCID 117864562, compound

Product 1

HCID 117859583HCID 117859583, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 375 mg (0.57 mmol, 57% purity) of 7-[(2,6-difluorobenzyl)oxy]-5-methoxy-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (Example 162A) in 8.0 ml of 1,4-dioxane was admixed with 6.0 ml of aqueous 2M sodium hydroxide solution. The mixture was stirred at 100° C. for a further 18 hours. The reaction mixture was concentrated under reduced pressure. The residue was admixed with 4 ml of acetonitrile and 2 ml of water, followed by 0.8 ml of trifluoroacetic acid. The resulting precipitate was filtered off and dried under reduced pressure, which gave 172 mg (65% yield, 75% purity) of product.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationThe resulting precipitate was filtered off
  3. customdried under reduced pressure, which
  4. customgave 172 mg (65% yield, 75% purity) of product

Sources & evidence

ORD record
ord-77cf241e187c47b8a3fcd3d5db269ede
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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