HCID 11670736, compound → HCID 11554821, compound

HRID 1693534Notes

Reaction equation

HRID 1693534 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][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])=[CH:4][CH:3]=1.[H][H]>O1CCOCC1.O.[Pt]=O>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([N:17]2[C:11]3[N:10]=[C:9]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=4[Cl:34])[N:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[C:13](=[O:14])[C:12]=3[CH:15]=[N:16]2)=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 11670736HCID 11670736, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11554821HCID 11554821, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

5-(4-Chloro-phenyl)-6-(2,4-dichloro-phenyl)-1-(4-nitro-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (100 mg, 0.195 mmol) is dissolved in 20 mL of dioxane. Platinumoxide (11.0 mg, 0.0484 mmol) was added as a slurry in 2 mL of water to the reaction mixture under a nitrogen atmosphere. The mixture was placed under balloon pressure of hydrogen and the reaction is completed within 1 h. The solids are filtered off and the solution is concentrated. Purification by reverse phase HPLC affords the title compound. 1H NMR (DMSO, 400 MHz) δ 8.78 (s, 1H), 8.15 (d, 2H), 7.97-7.95 (m, 2H), 7.90 (m, 3H), 7.84 (dd, 1H), 7.78 (m, 1H), 7.30 (d, 2H), 6.00 (s, 2H). HPLC-MS calculated for C23H14Cl3N5O (M+H+) 482.0. Found: 482.0.

Workup

  1. filtrationThe solids are filtered off
  2. concentrationthe solution is concentrated
  3. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-db098348e136409389de776e4b1d0545
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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