Hydrochloric Acid → 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid

HRID 1253535Notes

Reaction equation

HRID 1253535 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]([O:20]CC)=[O:19])[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.[OH-].[Na+].Cl>CO.O1CCOCC1.O>[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]([OH:20])=[O:19])[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide3×HCID 67374371Ethyl 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

Product 1

HCID 584048684-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

Ethyl 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylate (532 mg, 1.77 mmol) was dissolved in methanol (2 ml)/1,4-dioxane (2 ml)/Water (2 ml), then 1 N aqueous sodium hydroxide (1.77 ml, 1.77 mmol) was added and the mixture was heated to 55° C. After 2 h, LCMS analysis indicated incomplete conversion. Additional 1 N aqueous sodium hydroxide (0.18 ml, 0.18 mmol) was added and the reaction mixture was stirred for 1 h. LCMS analysis indicated incomplete conversion, so additional 1 N aqueous sodium hydroxide (0.18 ml, 0.18 mmol) was added and the reaction mixture was stirred overnight at 55° C. The reaction mixture was cooled to ambient temperature and 1N HCl (2.12 ml, 2.12 mmol) was added. The mixture was concentrated to give a tan solid that was suspended in 10 mL of water, filtered, and washed with water. The solid was transferred to a flask as a slurry in methanol and concentrated to give 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carboxylic acid.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred overnight at 55° C
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. concentrationThe mixture was concentrated
  5. customto give a tan solid
  6. filtrationfiltered
  7. washwashed with water
  8. customThe solid was transferred to a flask as a slurry in methanol
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-984cfe5421ac48d2a16fa2e5b667fdab
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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