Hydrazine hydrate (1:1) → HCID 11662711, compound

HRID 1693516Notes

Reaction equation

HRID 1693516 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)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.O.[NH2:38]N>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][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[NH:38][N:32]=[CH:31][N:30]=3)=[CH:26][CH:25]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57897905HCID 57897905, compound

Product 1

HCID 11662711HCID 11662711, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-[5-(4-chloro-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-N-dimethylaminomethylene-benzamide (7.0 mg, 0.014 mmol) and hydrazine hydrate (5 mg, 0.1 mmol) in acetic acid (200 μL) is stirred at 90° C. for 1 h and cooled down to room temperature. The solvent is removed under vacuum and 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, 2% MeOH/CH2Cl2) to provide the titled compound 5-(4-chloro-phenyl)-1-phenyl-6-[4-(2H-[1,2,4]triazol-3-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as white solid (4.8 mg, 73%). 1H NMR (CDCl3) δ(ppm) 8.40(s, 1H), 8.34(s, 1H), 8.15(d, 2H), 8.03(d, 2H), 7.51(t, 2H), −7.45 (d, 2H), 7.34 (t, 1H), 7.31(d, 2H), 7.11(d, 2H); HPLC-MS calculated for C25H16ClN7O (M+H+): 466.1. Found: 466.1.

Workup

  1. temperaturecooled down to room temperature
  2. customThe solvent is removed under vacuum and residue
  3. additionis 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, 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-e21c706207a54447a9241165ab0e965f
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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