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

HRID 1522452Notes

Reaction equation

HRID 1522452 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:20]([O:22]CC)=[O:21])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]4)[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>>[CH:14]1([N:10]2[C:8]3[N:9]=[C:4]([CH:1]4[CH2:2][CH2:3]4)[CH:5]=[C:6]([C:20]([OH:22])=[O:21])[C:7]=3[C:12]([CH3:13])=[N:11]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 67124309Ethyl 1-cyclohexyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 671244651-cyclohexyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Procedure

The title compound was prepared in the same manner as described for intermediate 52 using ethyl 6-cyclopropyl-1-(1-cyclohexyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (820 mg, 2.5 mmol) and sodium hydroxide (7.51 mL, 7.51 mmol). The final product was collected as a solid, 0.660 g (88%). LCMS E-S (M+H)=300.4 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01-1.11 (m, 4 H), 1.16-1.31 (m, 1 H), 1.36-1.55 (m, 2 H), 1.70 (d, J=12.38 Hz, 1 H), 1.80-1.98 (m, 6 H), 2.32 (m, J=7.80, 7.80, 5.05, 4.86 Hz, 1 H), 2.55 (s, 3 H), 4.60-4.73 (m, 1 H), 7.40 (s, 1 H), 13.71 (br. s., 1 H).

Workup

  1. customThe final product was collected as a solid, 0.660 g (88%)

Sources & evidence

ORD record
ord-a12bb71e4fc043e4810f633c0313afff
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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