Bromobenzene → HCID 57672140, compound

HRID 548573Notes

Reaction equation

HRID 548573 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[CH:22]=[N:21][CH:20]=[CH:19][N:18]=1.BrC1C=CC=CC=1>COC(C)(C)C>[N:18]1[CH:19]=[CH:20][N:21]=[CH:22][C:17]=1[NH:16][C:10]([C:4]1[C:3](=[O:15])[N:2]([CH3:1])[C:7]([CH3:8])=[CH:6][C:5]=1[OH:9])=[O:12]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 78747AminopyrazineHCID 57619607Ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 57672140HCID 57672140, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

211 mg of ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate and 95 mg of aminopyrazine were added to 6 ml of bromobenzene, and the mixture was stirred for 3 hours under the heat-refluxing condition. The reaction mixture was cooled to room temperature, and t-butyl methyl ether was added to the mixture. The resulting solid was collected by filtration, washed with t-butyl methyl ether, and dried to obtain 258 mg of N-(2-pyrazinyl)-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide (hereinafter, referred to as present compound 1) represented by the formula:

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with t-butyl methyl ether
  3. customdried

Sources & evidence

ORD record
ord-2671e7ac9d4f4aa28ae62c801dfbb121
Source dataset
uspto-grants-2011_05
Patent number
US07943614B2

Reaction notes

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