Pyridine → HCID 23077743, compound

HRID 1349507Notes

Reaction equation

HRID 1349507 reaction equation
[NH2:1][C:2]1[C:3](=[O:30])[C:4]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:5]2[C:10](=[O:11])[N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)[CH2:8][CH2:7][N:6]2[CH:21]=1.N1C=CC=CC=1.[C:37](Cl)(=[O:41])[CH:38]([CH3:40])[CH3:39].S([O-])(O)(=O)=O.[K+]>C(Cl)(Cl)Cl>[CH2:23]([O:22][C:4]1[C:3](=[O:30])[C:2]([NH:1][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])=[CH:21][N:6]2[CH2:7][CH2:8][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)[C:10](=[O:11])[C:5]=12)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 516920Potassium bisulfateHCID 23077599HCID 23077599, compound

Product 1

HCID 23077743HCID 23077743, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 7-amino-9-benzyloxy-2-(3-chloro-4-fluorobenzyl)-3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,8-dione (29 mg) in chloroform (0.6 ml) were added pyridine (0.0082 ml) and isobutyryl chloride (0.01 ml) at 0° C., and the mixture was stirred at room temperature for 1.5 hr. 5% Aqueous potassium hydrogen sulfate solution was added and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was dried, concentrated and purified by silica gel thin layer chromatography (chloroform:methanol=10:1) to give N-[9-benzyloxy-2-(3-chloro-4-fluorobenzyl)-1,8-dioxo-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrazin-7-yl]isobutyramide (29 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe obtained ethyl acetate layer was dried
  3. concentrationconcentrated
  4. custompurified by silica gel thin layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-cfbd59d4c3c74a309d558e145774fa78
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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