Sodium Hydroxide → 6-Cyclopropyl-1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522446Notes

Reaction equation

HRID 1522446 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:23]([O:25]CC)=[O:24])[C:7]3[CH:12]=[N:11][N:10]([CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:23]([OH:25])=[O:24])[C:7]3[CH:12]=[N:11][N:10]([CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68078825Ethyl 6-cyclopropyl-1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 680785376-Cyclopropyl-1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-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 6-cyclopropyl-1-[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (110 mg, 0.294 mmol), sodium hydroxide (1 mL, 0.294 mmol), and ethanol (10 mL) wherein the stir time was 16 h. The final product was collected as 0.060 g (59%). LCMS E-S (M+H)=347.1 1H NMR (400 MHz, DMSO-d6) δ ppm 1.06-1.13 (m, 4 H) 1.27 (s, 9 H) 2.33-2.43 (m, 1 H) 3.37 (q, J=5.81 Hz, 2 H) 4.44 (t, J=5.94 Hz, 2 H) 6.84 (t, J=5.81 Hz, 1 H) 7.62 (s, 5 H) 8.24 (s, 1 H).

Workup

  1. customThe final product was collected as 0.060 g (59%)

Sources & evidence

ORD record
ord-bb3ae4e4752d4a96b1a53fe46a88d0df
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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