2-Methylimidazole → 2-[(2-Methylimidazol-1-yl)-methyl]-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine

HRID 2086895Notes

Reaction equation

HRID 2086895 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]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)[CH:11]=2)[C:6]2[N:27]=[CH:28][CH:29]=[CH:30][C:5]=2[N:4]=1.[CH3:31][C:32]1[NH:33][CH:34]=[CH:35][N:36]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:31][C:32]1[N:33]([CH2:2][C:3]2[C:8](=[O:9])[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17](=[O:26])[C:18]4[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=4)[CH:11]=3)[C:6]3[N:27]=[CH:28][CH:29]=[CH:30][C:5]=3[N:4]=2)[CH:34]=[CH:35][N:36]=1

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 516892Sodium BicarbonateHCID 227245262-Bromomethyl-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine

Product 1

HCID 227245032-[(2-Methylimidazol-1-yl)-methyl]-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazineYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of 2-bromomethyl-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (105 mg) and 2-methylimidazole (171 mg) in N,N-dimethylformamide (10 ml) was stirred for 3 hours at 70° C. and 1 hour at 80° C. The mixture was poured into aqueous sodium hydrogencarbonate and extracted by ethyl acetate (100 ml). The organic layer was evaporated and chromatographed to obtain 2-[(2-methylimidazol-1-yl)-methyl]-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (50 mg) in brown powder form.

Workup

  1. extractionextracted by ethyl acetate (100 ml)
  2. customThe organic layer was evaporated
  3. customchromatographed

Sources & evidence

ORD record
ord-9f7798044fe64e74a76cefdf8b72fc88
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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