Sodium Hydroxide → 1-(1,1-Dimethylethyl)-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 476111Notes

Reaction equation

HRID 476111 reaction equation
[CH3:1][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:12]=[C:13]([C:14]([O:16]CC)=[O:15])[C:8]=2[C:7]([CH3:27])=[N:6]1)([CH3:4])[CH3:3].[OH-].[Na+]>CCO>[CH3:4][C:2]([N:5]1[C:9]2[N:10]=[C:11]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:8]=2[C:7]([CH3:27])=[N:6]1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67124416Ethyl 1-(1,1-dimethylethyl)-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 680786021-(1,1-Dimethylethyl)-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 75 using ethyl 1-(1,1-dimethylethyl)-3-methyl-6-[4-(methyloxy)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (400 mg, 1.089 mmol), 3N sodium hydroxide (1.814 mL, 5.44 mmol), and EtOH (6 mL). The product was collected as 347 mg (94%). LCMS E-S (M+H)=340.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.81 (s, 9H), 2.55 (s, 3H), 7.11 (d, J=8.84 Hz, 2H), 7.89 (s, 1H), 8.16 (d, J=8.84 Hz, 2H).

Workup

  1. customThe product was collected as 347 mg (94%)

Sources & evidence

ORD record
ord-e3cf2a365f68454c8877d892d77de560
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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