HCID 86720055, compound → 2-[5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-(2,2,2-trifluoro ethyl)-7,9-dihydro-8H-purin-8-one

HRID 510133Notes

Reaction equation

HRID 510133 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:19]=[C:18]4[C:14]([N:15]([CH2:21][C:22]([F:25])([F:24])[F:23])[C:16](=[O:20])[NH:17]4)=[C:13](I)[N:12]=3)=[N:9][N:8]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[C:5]2=[N:6][CH:7]=1>CN(C)C=O.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:19]=[C:18]4[C:14]([N:15]([CH2:21][C:22]([F:24])([F:23])[F:25])[C:16](=[O:20])[NH:17]4)=[CH:13][N:12]=3)=[N:9][N:8]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 86720055HCID 86720055, compound

Product 1

HCID 666139052-[5-Fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-(2,2,2-trifluoro ethyl)-7,9-dihydro-8H-purin-8-oneYield 32.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, 161 mg (0.275 mmol) of the compound from example 131 were dissolved in 15 ml of dimethylformamide, admixed with 100 mg of 10% palladium on charcoal and hydrogenated under standard hydrogen pressure overnight. The reaction mixture was filtered through Celite and concentrated, and the residue was purified by means of preparative HPLC (eluent: water/acetonitrile/water with 1% trifluoroacetic acid, gradient 65:30:5→0:95:5). 41 mg of the title compound were obtained (33% of theory).

Workup

  1. custompressure overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. customthe residue was purified by means of preparative HPLC (eluent: water/acetonitrile/water with 1% trifluoroacetic acid, gradient 65:30:5→0:95:5)

Sources & evidence

ORD record
ord-2781129d35ed4835ad19261c88cb9626
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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