Bromobenzene → HCID 57619637, compound

HRID 545283Notes

Reaction equation

HRID 545283 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([C:10]([O:12]CC)=O)[C:3]1=[O:15].[NH2:16][C:17]1[NH:18][CH:19]=[CH:20][N:21]=1.BrC1C=CC=CC=1>>[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([C:10]([NH:16][C:17]2[NH:18][CH:19]=[CH:20][N:21]=2)=[O:12])[C:3]1=[O:15]

Participants

4

Reactant 3

HCID 7961BromobenzeneHCID 821402-AminoimidazoleHCID 57619607Ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate2×

Product 1

HCID 57619637HCID 57619637, compoundYield 192%

Procedure

257 mg of ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxyl ate and 260 mg of 2-aminoimidazole were added to 5 ml of bromobenzene, then, the mixture was stirred for 2 hours under heat refluxing condition. Further, to the mixture was added 151 mg of ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxyl ate, and the resultant mixture was stirred for 2.5 hours under heat refluxing condition. The reaction mixture was cooled to room temperature. The resulting solid was collected by filtration, and washed with a mixed solvent of t-butyl methyl ether and hexane and dried to obtain 580 mg of 1,6-dimethyl-4-hydroxy-N-(2-imidazolyl)-2-oxo-1,2-dihydropy ridine-3-carboxamide (hereinafter, referred to as present compound 26) represented by the formula:

Workup

  1. temperatureunder heat
  2. temperaturerefluxing condition
  3. temperatureunder heat
  4. temperaturerefluxing condition
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with a mixed solvent of t-butyl methyl ether and hexane
  7. customdried

Sources & evidence

ORD record
ord-f12d7f01380c4da5be673967b94b2f2f
Source dataset
uspto-grants-2011_05
Patent number
US07935716B2

Reaction notes

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