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

HRID 476056Notes

Reaction equation

HRID 476056 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([CH:20]4[CH2:22][CH2:21]4)[CH:13]=[C:14]([C:15]([O:17]CC)=[O:16])[C:9]=3[C:8]([CH3:23])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([CH:20]4[CH2:21][CH2:22]4)[CH:13]=[C:14]([C:15]([OH:17])=[O:16])[C:9]=3[C:8]([CH3:23])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67124342ethyl 1-cyclopentyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 671241831-Cyclopentyl-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-cyclopentyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (740 mg, 2.361 mmol), sodium hydroxide (4 ml, 4.00 mmol), and ethanol (30 mL), wherein the stir time was 1 h. The final product was collected as 0.530 g (79%). LCMS E-S (M+H)=286.3 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96-1.12 (m, 4H) 1.52-1.74 (m, 2H) 1.82-2.13 (m, 6H) 2.26-2.37 (m, 1H) 2.55 (s, 3H) 5.17-5.30 (m, 1H) 7.43 (s, 1H) 13.70 (br. s., 1H).

Workup

  1. customThe final product was collected as 0.530 g (79%)

Sources & evidence

ORD record
ord-09f6b22b3984409ea927b1b27468d8c1
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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