Chloroform → HCID 54705341, compound

HRID 1349505Notes

Reaction equation

HRID 1349505 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[CH2:6][N:7]1[CH:12]=[CH:11][N:10]2[CH:13]=[C:14]([NH:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:15](=[O:18])[C:16]([OH:17])=[C:9]2[C:8]1=[O:24].C(Cl)(Cl)Cl.[C:32](Cl)(=[O:34])[CH3:33].S([O-])(O)(=O)=O.[K+]>N1C=CC=CC=1>[Cl:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][CH:27]=1)[CH2:6][N:7]1[CH:12]=[CH:11][N:10]2[CH:13]=[C:14]([N:19]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:32](=[O:34])[CH3:33])[C:15](=[O:18])[C:16]([OH:17])=[C:9]2[C:8]1=[O:24]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6367Acetyl chlorideHCID 516920Potassium bisulfateHCID 54683475HCID 54683475, compound

Product 1

HCID 54705341HCID 54705341, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(3-Chlorobenzyl)-9-hydroxy-7-isobutylamino-2H-pyrido[1,2-a]pyrazine-1,8-dione hydrochloride (23 mg) was added to chloroform (2 ml), and pyridine (0.062 ml) and acetyl chloride (0.024 ml) were successively added at 0° C. The mixture was stirred at room temperature for 2 hr. 5% Aqueous potassium hydrogen sulfate solution was added to the obtained reaction mixture, and the mixture was extracted with ethyl acetate. The solvent was evaporated and the obtained residue was dissolved in tetrahydrofuran (0.5 ml)-methanol (0.1 ml), and 1N aqueous sodium hydroxide solution (0.084 ml) was added. The mixture was stirred at room temperature for 30 min. 2N Aqueous hydrochloric acid (0.056 ml) was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried and concentrated. Crystallization from ethyl acetate-diisopropyl ether gave N-[2-(3-chlorobenzyl)-9-hydroxy-1,8-dioxo-1,8-dihydro-2H-pyrido[1,2-a]pyrazin-7-yl]-N-isobutylacetamide (18.2 mg).

Workup

  1. additionwere successively added at 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe solvent was evaporated
  4. dissolutionthe obtained residue was dissolved in tetrahydrofuran (0.5 ml)-methanol (0.1 ml), and 1N aqueous sodium hydroxide solution (0.084 ml)
  5. additionwas added
  6. stirringThe mixture was stirred at room temperature for 30 min
  7. addition2N Aqueous hydrochloric acid (0.056 ml) was added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with saturated brine
  10. customdried
  11. concentrationconcentrated
  12. customCrystallization from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-82feeea007d54f9bb46c58b222c2875b
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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