Sodium Hydroxide → 6-Cyclopropyl-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522454Notes

Reaction equation

HRID 1522454 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][O:17][CH2:16][CH2:15]4)[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[CH:1]1([C:4]2[CH:5]=[C:6]([C:20]([OH:22])=[O:21])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68079246Ethyl 6-cyclopropyl-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 680831046-Cyclopropyl-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an EtOH solution (30 mL) of ethyl 6-cyclopropyl-3-methyl-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (300 mg, 0.911 mmol) was added sodium hydroxide (1.82 mL, 1.82 mmol) and the mixture stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was dissolved in 20 mL of water. The contents were acidifed with acetic acid, and extracted with EtOAc (4×30 mL). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the final product as 265 mg (97%). LCMS E-S (M+H)=302.4 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.09 (m, 4 H), 1.81 (dd, J=12.38, 2.27 Hz, 2 H), 2.15 (qd, J=12.25, 4.42 Hz, 2 H), 2.28-2.37 (m, 1 H), 2.54 (s, 3 H), 3.46-3.60 (m, 2 H), 3.89-4.02 (m, 2 H), 4.91 (m, J=11.56, 11.56, 4.17, 4.04 Hz, 1 H), 7.42 (s, 1 H), 13.73 (br. s., 1 H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 20 mL of water
  3. extractionextracted with EtOAc (4×30 mL)
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67e63f486a314c4fb1a9819aec8e2f8c
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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