Sodium Hydroxide → 3-Methyl-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522488Notes

Reaction equation

HRID 1522488 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([C:11]([O:13]CC)=[O:12])=[CH:8][C:7]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[N:6][C:5]=2[N:4]([CH:22]([CH3:24])[CH3:23])[N:3]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[C:10]2[C:9]([C:11]([OH:13])=[O:12])=[CH:8][C:7]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[N:6][C:5]=2[N:4]([CH:22]([CH3:24])[CH3:23])[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67124410Ethyl 3-methyl-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 671244223-Methyl-1-(1-methylethyl)-6-(4-pyridinyl)-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 58 using ethyl 3-methyl-1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (36 mg, 0.111 mmol), Ethanol (2 ml) and sodium hydroxide (0.185 mL, 0.555 mmol). The final product was collected as 26 mg 79%). LCMS E-S (M+H)=297.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54 (d, J=6.4 Hz, 6 H), 2.65 (s, 3 H), 5.35 (m, 1 H), 8.17 (s, 1 H) 8.24 (m, 2 H), 8.78 (m, 2 H).

Workup

  1. customThe final product was collected as 26 mg 79%)

Sources & evidence

ORD record
ord-e05da5dcfb184b38aa3f18ebb59bb263
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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