2-Methylimidazole → HCID 22724155, compound

HRID 2231063Notes

Reaction equation

HRID 2231063 reaction equation
Br[CH2:2][C:3]1[C:8](=[O:9])[N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2)[C:6]2[N:20]=[CH:21][CH:22]=[CH:23][C:5]=2[N:4]=1.[CH3:24][C:25]1[NH:26][CH:27]=[CH:28][N:29]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:19][O:18][C:16]([C:12]1[CH:11]=[C:10]([N:7]2[C:8](=[O:9])[C:3]([CH2:2][N:26]3[CH:27]=[CH:28][N:29]=[C:25]3[CH3:24])=[N:4][C:5]3[CH:23]=[CH:22][CH:21]=[N:20][C:6]2=3)[CH:15]=[CH:14][CH:13]=1)=[O:17]

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 516892Sodium BicarbonateHCID 22724073HCID 22724073, compound

Product 1

HCID 22724155HCID 22724155, compoundYield 0.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromomethyl-4-(3-methoxycarbonylphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (1.22 g) and 2-methylimidazole (1.35 g) in N,N-dimethylformamide (10 ml) was stirred at 80° C. for 1 hour. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic solution was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (5% methanol in chloroform) to give 4-(3-methoxycarbonylphenyl)-2-[(2-methylimidazol-1-yl)methyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (15 4 mg).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic solution was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel column (5% methanol in chloroform)

Sources & evidence

ORD record
ord-1494ea89847e45c19a7c8b916fc2a72b
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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