Sodium Hydroxide → HCID 67124533, compound

HRID 476061Notes

Reaction equation

HRID 476061 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:21]([O:23]CC)=[O:22])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:19][CH2:18][N:17]([CH3:20])[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:21]([OH:23])=[O:22])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]4[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]4)[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68078649HCID 68078649, compound

Product 1

HCID 67124533HCID 67124533, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To an EtOH solution (10 mL) of ethyl 6-cyclopropyl-3-methyl-1-(1-methyl-4-piperidinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (620 mg, 1.811 mmol) was added sodium hydroxide (5.43 mL, 5.43 mmol) and the mixture heated at 70° C. for 1 hour. The solvent was removed in vacuo and the residue was dissolved in 20 mL of water. The contents were acidified 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 a minor amount of product. The aqueous phase was concentrated in vacuo and the crude residue purified by reverse phase HPLC purification (eluent: 0% ACN/H2O, 0.1% TFA to 45% ACN/H2O, 0.1% TFA). The isolated solid product was concentrated from toluene to afford the final product as 510 mg (90%). LCMS E-S (M+H)=315.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (d, J=6.57 Hz, 4H), 2.10 (d, J=13.14 Hz, 2H), 2.30-2.42 (m, 3H), 2.55 (s, 3H), 2.77-2.92 (m, 3H), 3.30 (br. s., 2H), 3.57 (d, J=12.13 Hz, 2H), 4.98 (m, J=11.78, 11.78, 3.85, 3.66 Hz, 1H), 7.46 (s, 1H), 9.87 (br. s., 1H).

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
  8. customto afford a minor amount of product
  9. concentrationThe aqueous phase was concentrated in vacuo
  10. customthe crude residue purified by reverse phase HPLC purification (eluent: 0% ACN/H2O, 0.1% TFA to 45% ACN/H2O, 0.1% TFA)
  11. concentrationThe isolated solid product was concentrated from toluene

Sources & evidence

ORD record
ord-e208a32bb64143519d269a7ad4ce7f11
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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