Hydrochloric Acid → HCID 89618449, compound

HRID 2167761Notes

Reaction equation

HRID 2167761 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]1[CH:21]=[CH:20][N:19]2[N:22]=[CH:23][C:24]([C:25]([O:27]CC)=[O:26])=[C:18]2[CH:17]=1.Cl>CO.C1COCC1.O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[CH:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]1[CH:21]=[CH:20][N:19]2[N:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[C:18]2[CH:17]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89618753HCID 89618753, compound

Product 1

HCID 89618449HCID 89618449, compoundYield 39.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

5N aqueous solution of NaOH (2 mL) was added to stirred solution of ethyl 5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (50 mg, 0.134 mmol) in a mixture of MeOH (4 mL) and THF (4 mL) and continued stirring at 80° C. for 4 h. The reaction mixture was concentrated under reduced pressure to afford the crude product. The crude product thus obtained was diluted with cold water, acidified with concentrated HCl solution to obtain a solid precipitate. This solid precipitate was filtered and dried well to afford 18 mg of 5-(2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid as off white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto afford the crude product
  3. customThe crude product thus obtained
  4. customto obtain a solid precipitate
  5. filtrationThis solid precipitate was filtered
  6. customdried well

Sources & evidence

ORD record
ord-c47ee83b365a44cc9c271e2d485536a3
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Reaction notes

Loading…