Sodium Hydroxide → HCID 57675146, compound

HRID 490899Notes

Reaction equation

HRID 490899 reaction equation
[OH-].[Na+].[CH2:3]([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([C:22]([O:24]CC)=[O:23])[C:13]([N:14]([CH3:21])[CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:8]2[CH:7]=[N:6]1)[CH3:4]>C(O)C>[CH2:3]([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([C:22]([OH:24])=[O:23])[C:13]([N:14]([CH3:21])[CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[C:8]2[CH:7]=[N:6]1)[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 44561082Ethyl 1-ethyl-4-[methyl(tetrahydro-2H-pyran-4-yl)amino]-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 57675146HCID 57675146, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Sodium hydroxide (0.43 g, 10.8 mmol) was added to a solution of Intermediate 51 in ethanol (10 ml, 95%). The reaction mixture was heated at 50° C. for 18 hours. The solvent was evaporated in vacuo and the residue dissolved in water and acidified to pH 3 by the addition of aqueous hydrochloric acid. The solution was extracted with DCM. The organic phase was separated using a hydrophobic frit (Whatman PTFE Folter Media with Polypropylene Housing 5 μM pore size) and the solvent evaporated in vacuo to give Intermediate 52 as a white solid (0.65 g). LCMS showed MH+=305; TRET=1.97 min.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in water
  3. additionacidified to pH 3 by the addition of aqueous hydrochloric acid
  4. extractionThe solution was extracted with DCM
  5. customThe organic phase was separated
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-0d8a73ae84d1417992126827824f5ef2
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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