HCID 54707546, compound → HCID 54676292, compound

HRID 2109847Notes

Reaction equation

HRID 2109847 reaction equation
C([O:8][CH2:9][CH:10]1[N:15]2[C:16](=[O:22])[CH:17]=[C:18]([OH:21])[C:19]([OH:20])=[C:14]2[C:13](=[O:23])[N:12]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:11]1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][CH2:9][CH:10]1[N:15]2[C:16](=[O:22])[CH:17]=[C:18]([OH:21])[C:19]([OH:20])=[C:14]2[C:13](=[O:23])[N:12]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[CH2:11]1

Participants

4

Reactant 1

HCID 54707546HCID 54707546, compound

Product 1

HCID 54676292HCID 54676292, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[(benzyloxy)methyl]-2-(4-fluorobenzyl)-8,9-dihydroxy-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-dione (151 mg) and 5% Pd/C (57 mg) in ethanol (20 mL) was stirred under an atmosphere of hydrogen (1 atm) at room temperature overnight. The product mixture was filtered through a pad of Celite, and concentrated under vacuum. The residue was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

  1. filtrationThe product mixture was filtered through a pad of Celite
  2. concentrationconcentrated under vacuum
  3. customThe residue was subjected to HPLC purification on C-18 stationary phase
  4. washeluted with water/acetonitrile/TFA mobile phase
  5. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-1f3ea4bee0b24e3e9f9020ea10078887
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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