Sodium Hydroxide → 6-cyclopropyl-1-propyl-1H-pyrazolo(3,4-b)pyridine-4-carboxylic acid

HRID 476051Notes

Reaction equation

HRID 476051 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:13]([O:15]CC)=[O:14])[C:7]3[CH:12]=[N:11][NH:10][C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[H-].[Na+].I[CH2:21][CH2:22][CH3:23].[OH-].[Na+]>CN(C=O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[C:7]3[CH:12]=[N:11][N:10]([CH2:21][CH2:22][CH3:23])[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 67124108ethyl 6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 196165146-cyclopropyl-1-propyl-1H-pyrazolo(3,4-b)pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as in the same manner as described for intermediate 43 using ethyl 6-cyclopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (200 mg, 0.865 mmol), sodium hydride (29.1 mg, 1.211 mmol), DMF (10 mL), 1-iodopropane (162 mg, 0.951 mmol), and NaOH (1 mL). The crude product was purified by silica gel chromatography (eluent: 0 to 10% MeOH:DCM) to afford the final product as a solid, 90 mg (42%). Regiochemical assignment supported by 2D HNMR. LCMS E-S (M+H)=246.0 1H NMR (400 MHz, DMSO-d6) δ ppm 13.83 (br s, 1H), 8.24 (s, 1H), 7.62 (s, 1H), 4.26 (t, 2H, J=7.2 Hz), 2.37-2.40 (m, 2H), 1.83-1.89 (m, 2H), 1.07-1.11 (m, 4H), 0.77 (t, 3H, J=7.2 Hz).

Workup

  1. customThe title compound was prepared as in the same manner
  2. customThe crude product was purified by silica gel chromatography (eluent: 0 to 10% MeOH:DCM)

Sources & evidence

ORD record
ord-828c6f565dfa44209a3cad8799211dda
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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