Bromobenzene → 1,6-dimethyl-4-hydroxy-N-(5-methylthiazol-2-yl)-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 545277Notes

Reaction equation

HRID 545277 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[S:18][C:19]([CH3:22])=[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[S:18][C:19]([CH3:22])=[CH:20][N:21]=2)=[O:12])[C:3]1=[O:15]

Participants

4

Reactant 3

HCID 7961BromobenzeneHCID 3517702-Amino-5-methylthiazoleHCID 57619607Ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 576196381,6-dimethyl-4-hydroxy-N-(5-methylthiazol-2-yl)-2-oxo-1,2-dihydropyridine-3-carboxamideYield 73.2%

Procedure

212 mg of ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxyl ate and 105 mg of 2-amino-5-methylthiazole were added to 2.5 ml of bromobenzene, then, the mixture was stirred for 5.5 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 188 mg of 1,6-dimethyl-4-hydroxy-N-(5-methylthiazol-2-yl)-2-oxo-1,2-d ihydropyridine-3-carboxamide (hereinafter, referred to as present compound 20) represented by the formula:

Workup

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

Sources & evidence

ORD record
ord-11ac0c7aca454eac9f129fcf0a70ea6f
Source dataset
uspto-grants-2011_05
Patent number
US07935716B2

Reaction notes

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