Sodium Hydroxide → HCID 178434033, compound

HRID 1522330Notes

Reaction equation

HRID 1522330 reaction equation
[OH-].[Na+].[CH3:3][C:4]([N:7]1[C:11]2[NH:12][C:13](=[O:21])[CH:14]=[C:15]([C:16]([O:18]CC)=[O:17])[C:10]=2[C:9]([CH3:22])=[N:8]1)([CH3:6])[CH3:5]>CCO>[CH3:6][C:4]([N:7]1[C:11]2[N:12]=[C:13]([OH:21])[CH:14]=[C:15]([C:16]([OH:18])=[O:17])[C:10]=2[C:9]([CH3:22])=[N:8]1)([CH3:3])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136334041HCID 136334041, compound

Product 1

HCID 178434033HCID 178434033, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (52.6 mL, 52.6 mmol) was added to an EtOH solution (100 mL) of ethyl 1-(1,1-dimethylethyl)-3-methyl-6-oxo-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (7.3 g, 26.3 mmol) and stirred at room temperature for 16 h. The solvent was removed in vacuo. The crude residue was suspended in water, and extracted with EtOAc. The combined organic layers were washed with water, dried over MgSO4, filtered, and concentrated in vacuo. The solid product obtained was set aside. The aqueous phase was concentrated in vacuo and the crude product purified by reverse phase HPLC (mobile phase: 20-50% ACN/H2O, 0.1% TFA) to afford additional product. The combined products were collected as a solid, 5.76 g (88%). LCMS E-S (M+H)=250.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.5-13.9 (br s, 1H), 11.2-11.5 (br s, 1H), 6.78 (s, 1H), 2.46 (s, 3H), 1.70 (s, 9H).

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe solid product obtained
  8. concentrationThe aqueous phase was concentrated in vacuo
  9. customthe crude product purified by reverse phase HPLC (mobile phase: 20-50% ACN/H2O, 0.1% TFA)
  10. customto afford additional product
  11. customThe combined products were collected as a solid, 5.76 g (88%)

Sources & evidence

ORD record
ord-9aa347b623be4704a0b1177b44bc1631
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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