Sodium Hydroxide → HCID 117859562, compound

HRID 1486327Notes

Reaction equation

HRID 1486327 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]([CH2:25][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]([CH2:25][CH3:26])[CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117864695HCID 117864695, compound

Product 1

HCID 117859562HCID 117859562, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 287 mg (0.54 mmol, 70% purity) of 7-[(2,6-difluorobenzyl)oxy]-5-ethyl-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (Example 167A) in 5.5 ml of 1,4-dioxane was admixed with 2.7 ml of aqueous 2M sodium hydroxide solution. The mixture was stirred at 90° C. for a further 18 hours. The reaction mixture was concentrated under reduced pressure. The residue was admixed with water and the pH was adjusted to 7. The resulting precipitate was filtered off and dried under reduced pressure, which gave 280 mg (35% yield, 23% purity) of product, which were used in the next step without purification.

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 280 mg (35% yield, 23% purity) of product, which
  5. customwere used in the next step without purification

Sources & evidence

ORD record
ord-77c50cef31c944d499aa582f58bbeb94
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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