Hydrochloric Acid → 6-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 2279108Notes

Reaction equation

HRID 2279108 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[C:20]([CH3:21])=[N:19][NH:18][C:7]=2[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)[CH:10]=1)=[O:4].[OH-:22].[Na+].Cl>C(O)(C)C>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[CH:10]=[C:5]([C:3]([OH:2])=[O:4])[C:6]3[C:20]([CH3:21])=[N:19][N:18]([CH:7]4[CH2:6][CH2:5][CH2:10][CH2:9][O:22]4)[C:7]=3[N:8]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178497272HCID 178497272, compound

Product 1

HCID 1363597706-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 6-(4-hydroxy-phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid methyl ester (10.9 g) and sodium hydroxide solution (1N, 80 mL) in isopropanol (80 mL) was stirred at r.t. for 90 min. The pH was adjusted to 3 with 1N HCl and the mixture was poured onto water. The precipitate formed was filtered off and dried in air to give 6-(4-Hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (10.2 g, 97% yield).

Workup

  1. additionthe mixture was poured onto water
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. customdried in air

Sources & evidence

ORD record
ord-ef3e6c9224fb43c5b3c1a4a3e3c0181a
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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