2-Methylimidazole → HCID 22724155, compound

HRID 2086887Notes

Reaction equation

HRID 2086887 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 12.6%

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 (154 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-0999185b173d42a08b70358bdc889f3e
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

Loading…