HCID 13606798, compound → HCID 13606800, compound

HRID 652738Notes

Reaction equation

HRID 652738 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:22])=[CH:7][N:8]3[C:15](=[O:16])[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][N:12]=[C:9]32)=[CH:4][CH:3]=1.[CH3:23][CH:24]([CH:28]([CH3:31])[CH2:29][CH3:30])[C:25](Cl)=[O:26]>N1C=CC=CC=1>[CH3:23][CH:24]([CH:28]([CH3:31])[CH2:29][CH3:30])[C:25]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:22])=[CH:7][N:8]3[C:15](=[O:16])[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][N:12]=[C:9]32)=[CH:4][CH:3]=1)=[O:26]

Participants

4

Reactant 2

HCID 13606798HCID 13606798, compoundHCID 20196487HCID 20196487, compound

Product 1

HCID 13606800HCID 13606800, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 10-amino-7-methyl-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (1.5 g) in pyridine (110 ml) was added 2,3-dimethylpentanoyl chloride (1.4 g) under ice cooling. After stirring for 2 hours at ambient temperature, the reaction mixture was concentrated in vacuo. The residue in chloroform (100 ml) was washed with water, a cold 1N hydrochloric acid and water in turn and dried over magnesium sulfate. After removal of the solvent, the residue was chromatographed on a silica gel column using chloroform as an eluent to give ethyl 10-(2,3-dimethylpentanoylamino)-7-methyl-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (1.94 g).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washThe residue in chloroform (100 ml) was washed with water
  3. dry with materiala cold 1N hydrochloric acid and water in turn and dried over magnesium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-2f7999dce24d42f68db5784f6ada2122
Source dataset
uspto-grants-1987_06
Patent number
US04673676

Reaction notes

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