Hydrochloric Acid → 4-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylic acid

HRID 2206135Notes

Reaction equation

HRID 2206135 reaction equation
[C:1]([N:5]1[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([O:14][CH3:15])[C:8]=2[C:7]([C:16]2[CH:17]=[C:18]([C:21]([O:23]C)=[O:22])[S:19][CH:20]=2)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+].Cl>O.C1COCC1>[C:1]([N:5]1[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([O:14][CH3:15])[C:8]=2[C:7]([C:16]2[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[S:19][CH:20]=2)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 117988460methyl 4-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylate

Product 1

HCID 1179879274-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylic acidYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-(1-tert-butyl-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxylate (1.88 g) in a mixed solvent of methanol (30 mL)/THF (30 mL)/water (25 mL) was added 1N aqueous sodium hydroxide solution (5.44 mL) at room temperature, and the mixture was stirred overnight at room temperature. To the reaction mixture was added 1N hydrochloric acid, and the mixture was concentrated under reduced pressure. The residue was washed with water, and dried in vacuum to give the title compound (1.50 g).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. washThe residue was washed with water
  3. customdried in vacuum

Sources & evidence

ORD record
ord-c84b0a9c4b3d4288b81c522000f252eb
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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