Sodium Hydroxide → 1-Cyclobutyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522447Notes

Reaction equation

HRID 1522447 reaction equation
[CH:1]1([N:5]2[C:9]3[N:10]=[C:11]([CH:19]4[CH2:21][CH2:20]4)[CH:12]=[C:13]([C:14]([O:16]CC)=[O:15])[C:8]=3[C:7]([CH3:22])=[N:6]2)[CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([N:5]2[C:9]3[N:10]=[C:11]([CH:19]4[CH2:20][CH2:21]4)[CH:12]=[C:13]([C:14]([OH:16])=[O:15])[C:8]=3[C:7]([CH3:22])=[N:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68079207Ethyl 1-cyclobutyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 671243571-Cyclobutyl-6-cyclopropyl-3-methyl-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 46 using ethyl 1-cyclobutyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (550 mg, 1.837 mmol), sodium hydroxide (3 ml, 3.00 mmol), and ethanol (30 mL) wherein the stir time was 1 h. The final product was collected as 0.490 g (98%). LCMS E-S (M+H)=272.5 1H NMR (400 MHz, DMSO-d6) δ ppm 1.03-1.10 (m, 4 H), 1.80-1.91 (m, 2 H), 2.26-2.43 (m, 3 H), 2.58 (s, 3 H), 2.59-2.71 (m, 2 H), 5.35 (dq, J=8.59, 8.42 Hz, 1 H), 7.44 (s, 1 H), 13.73 (br. s., 1 H).

Workup

  1. customThe final product was collected as 0.490 g (98%)

Sources & evidence

ORD record
ord-f0597fe7dac643f8a304d48f31c9ec5a
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

Loading…