Bromobenzene → N-(5-chlorothiazol-2-yl)-1,3-dimethyl-4-hydroxy-2-oxo-1,2-d ihydropyridine-3-carboxamide

HRID 545279Notes

Reaction equation

HRID 545279 reaction equation
[CH3:1][N:2]1[C:7](C)=[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]([Cl:22])=[CH:20][N:21]=1.Br[C:24]1C=CC=CC=1>>[Cl:22][C:19]1[S:18][C:17]([NH:16][C:10]([C:4]2([CH3:24])[CH:5]([OH:9])[CH:6]=[CH:7][N:2]([CH3:1])[C:3]2=[O:15])=[O:12])=[N:21][CH:20]=1

Participants

4

Reactant 3

HCID 7961BromobenzeneHCID 389422-Amino-5-chlorothiazoleHCID 57619607Ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 86628807N-(5-chlorothiazol-2-yl)-1,3-dimethyl-4-hydroxy-2-oxo-1,2-d ihydropyridine-3-carboxamide

Procedure

223 mg of ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxyl ate and 129 mg of 2-amino-5-chlorothiazole were added to 2.5 ml of bromobenzene, then, the mixture was stirred for 8.5 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 153 mg of N-(5-chlorothiazol-2-yl)-1,3-dimethyl-4-hydroxy-2-oxo-1,2-d ihydropyridine-3-carboxamide (hereinafter, referred to as present compound 22) 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-6579397258ce41e6bcb3a2cc52783bfe
Source dataset
uspto-grants-2011_05
Patent number
US07935716B2

Reaction notes

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