Sodium Hydroxide → HCID 11612433, compound

HRID 1693517Notes

Reaction equation

HRID 1693517 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:36]=[CH:35][C:27]([C:28]([N:30]=[CH:31][N:32](C)C)=[O:29])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.NO.Cl.[OH-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:36]=[CH:35][C:27]([C:28]3[O:29][N:32]=[CH:31][N:30]=3)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 57897905HCID 57897905, compound

Product 1

HCID 11612433HCID 11612433, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-[5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-N-dimethylaminomethylene-benzamide (10 mg, 0.02 mmol) in acetic acid (200 μL) is added a mixture of NH2OH.HCl (5 mg, 0.072 mmol) in NaOH (1M, 50 μL, 0.05 mmol)). The mixture is stirred at 90° C. for 1 h. and cooled down to room temperature. Solvent is removed under vacuum and the residue is treated with saturated aqueous NaHCO3 solution (1 mL) and extracted with EtOAc (3×2 mL). The organic layers are combined and concentrated. The residue is purified by preparative thin layer chromatography (silica gel, 30% EtOAc/hex) to provide the titled compound 5-(4-chloro-phenyl)-6-(4-[1,2,4]oxadiazol-5-yl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as white solid (8 mg, 85%). 1H NMR (CDCl3) δ(ppm) 8.50(s, 1H), 8.35(s, 1H), 8.12(d, 2H), 8.06(d, 2H), 7.48-7.54 (m, 4H), 7.37(t, 1H), 7.34(d, 2H), 7.11(d, 2H); HPLC-MS calculated for C25H16ClN6O2 (M+H+): 467.1. Found: 467.1.

Workup

  1. temperaturecooled down to room temperature
  2. customSolvent is removed under vacuum
  3. additionthe residue is treated with saturated aqueous NaHCO3 solution (1 mL)
  4. extractionextracted with EtOAc (3×2 mL)
  5. concentrationconcentrated
  6. customThe residue is purified by preparative thin layer chromatography (silica gel, 30% EtOAc/hex)

Sources & evidence

ORD record
ord-b04402998e4643f7965b7d3e39409f25
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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