2-(benzyloxy)-5-(4-fluorophenyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one → HCID 178515148, compound

HRID 1396504Notes

Reaction equation

HRID 1396504 reaction equation
C([O:8][C:9]1[CH:25]=[C:12]2[C:13](=[O:24])[N:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:15][CH2:16][N:11]2[N:10]=1)C1C=CC=CC=1>CCOC(C)=O.CN(C=O)C.[OH-].[OH-].[Pd+2]>[F:23][C:20]1[CH:19]=[CH:18][C:17]([N:14]2[CH2:15][CH2:16][N:11]3[N:10]=[C:9]([OH:8])[CH:25]=[C:12]3[C:13]2=[O:24])=[CH:22][CH:21]=1

Participants

5

Reactant 1

HCID 727147832-(benzyloxy)-5-(4-fluorophenyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one

Product 1

HCID 178515148HCID 178515148, compoundYield 88.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(benzyloxy)-5-(4-fluorophenyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (0.79 g, 2.34 mmol) in a mixture of AcOEt (30 mL) and DMF (30 mL) was hydrogenated in a H-Cube reactor (1.5 ml/min, 70 mm Pd(OH)2/C cartridge, full H2 mode, 80° C., 1 cycle). The solvents were evaporated in vacuo to yield 5-(4-fluorophenyl)-2-hydroxy-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one (0.51 g, 88% yield) as a white solid, that was used in the next step without further purification.

Workup

  1. customwas hydrogenated in a H-Cube reactor
  2. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-5f5fc78bbe05440da31705de3b2fbcb1
Source dataset
uspto-grants-2014_12
Patent number
US08901125B2

Reaction notes

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