Sodium Hydroxide → 1-(1-Methylethyl)-6-(3-thienyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522485Notes

Reaction equation

HRID 1522485 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[CH:11]=[C:12]([C:13]([O:15]CC)=[O:14])[C:7]=2[CH:6]=[N:5]1)[CH3:3].[OH-].[Na+]>C(O)C>[CH3:3][CH:2]([N:4]1[C:8]2[N:9]=[C:10]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[C:7]=2[CH:6]=[N:5]1)[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67124419Ethyl 1-(1-methylethyl)-6-(3-thienyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 671242341-(1-Methylethyl)-6-(3-thienyl)-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 1-(1-methylethyl)-6-(3-thienyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (400 mg, 1.268 mmol), Ethanol (5 mL) THF (1 mL), and sodium hydroxide (2.114 mL, 6.34 mmol). The final product was collected as 370 mg (100%). LCMS E-S (M+H)=287.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55 (d, J=6.8 Hz, 6 H), 5.34 (quin, J=6.6 Hz, 1 H), 7.72 (dd, J=5.0, 3.0 Hz, 1 H), 7.93 (dd, J=5.0, 1.3 Hz, 1 H), 8.15 (s, 1 H), 8.34 (s, 1 H), 8.49 (dd, J=3.0, 1.3 Hz, 1 H), 13.97 (s, 1 H).

Workup

  1. customThe final product was collected as 370 mg (100%)

Sources & evidence

ORD record
ord-1a41a9b2558643b797eeed9c03dcfecb
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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