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

HRID 2086896Notes

Reaction equation

HRID 2086896 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.[C:31]1([C:37]2[NH:38][CH:39]=[CH:40][N:41]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[C:31]1([C:37]2[N:41]([CH2:2][C:3]3[C:8](=[O:9])[N:7]([C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17](=[O:26])[C:18]5[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=5)[CH:11]=4)[C:6]4[N:27]=[CH:28][CH:29]=[CH:30][C:5]=4[N:4]=3)[CH:40]=[CH:39][N:38]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 695912-PhenylimidazoleHCID 516892Sodium BicarbonateHCID 227245262-Bromomethyl-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine

Product 1

HCID 227242822-[(2-Phenylimidazol-1-yl)methyl]-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazineYield 16.2%

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 (285 mg) and 2-phenylimidazole (734 mg) in N,N-dimethylformamide (30 ml) was stirred for 3 hours at 80° C. The mixture was poured into aqueous sodium hydrogencarbonate (150 ml) and extracted by ethyl acetate (150 mg). The organic layer was evaporated and chromatographed to obtain 2-[(2-phenylimidazol-1-yl)methyl]-4-[3-(3,5-dichlorobenzoylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (52 mg) in brown powder form.

Workup

  1. extractionextracted by ethyl acetate (150 mg)
  2. customThe organic layer was evaporated
  3. customchromatographed

Sources & evidence

ORD record
ord-7b27107a0a724550910e6c17a2d7e74e
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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