9-benzyloxy-2-(3-chlorobenzyl)-7-(2,2-dimethylbutyryl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione → 2-[(3-Chlorophenyl)methyl]-7-(2,2-dimethylbutanoyl)-9-hydroxy-3,4-dihydropyrido[1,2-a]pyrazine-1,8-dione

HRID 1349500Notes

Reaction equation

HRID 1349500 reaction equation
C([O:8][C:9]1[C:10](=[O:35])[C:11]([C:28](=[O:34])[C:29]([CH3:33])([CH3:32])[CH2:30][CH3:31])=[CH:12][N:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)[C:15](=[O:27])[C:14]=12)C1C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][N:16]1[CH2:17][CH2:18][N:13]2[CH:12]=[C:11]([C:28](=[O:34])[C:29]([CH3:32])([CH3:33])[CH2:30][CH3:31])[C:10](=[O:35])[C:9]([OH:8])=[C:14]2[C:15]1=[O:27]

Participants

3

Reactant 1

HCID 230774849-benzyloxy-2-(3-chlorobenzyl)-7-(2,2-dimethylbutyryl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione

Product 1

HCID 546833552-[(3-Chlorophenyl)methyl]-7-(2,2-dimethylbutanoyl)-9-hydroxy-3,4-dihydropyrido[1,2-a]pyrazine-1,8-dioneYield 71.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

9-Benzyloxy-2-(3-chlorobenzyl)-7-(2,2-dimethylbutyryl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (55 mg) was dissolved in trifluoroacetic acid (0.5 ml) and the mixture was stirred at room temperature for 30 min. The solvent was evaporated and toluene was added, and the mixture was concentrated, which operations were performed twice. Crystallization from chloroform-diisopropyl ether gave 2-(3-chlorobenzyl)-7-(2,2-dimethylbutyryl)-9-hydroxy-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (32 mg).

Workup

  1. customThe solvent was evaporated
  2. additiontoluene was added
  3. concentrationthe mixture was concentrated
  4. customCrystallization from chloroform-diisopropyl ether

Sources & evidence

ORD record
ord-1bfa144d9ff14d4d84e815ae5f37897e
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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