Bromobenzene → HCID 57672127, compound

HRID 548574Notes

Reaction equation

HRID 548574 reaction equation
[Cl:1][C:2]1[C:3]([OH:16])=[C:4]([C:11]([O:13]CC)=O)[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[CH3:8].[NH2:17][C:18]1[N:19]=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=1.BrC1C=CC=CC=1>CCCCCC>[Cl:24][C:21]1[N:20]=[N:19][C:18]([NH:17][C:11]([C:4]2[C:5](=[O:10])[N:6]([CH3:9])[C:7]([CH3:8])=[C:2]([Cl:1])[C:3]=2[OH:16])=[O:13])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 216436-Amino-3-chloropyridazineHCID 57619613HCID 57619613, compound

Product 1

HCID 57672127HCID 57672127, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

168 mg of ethyl 5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate and 82 mg of 3-amino-6-chloropyridazine were added to 1.5 ml of bromobenzene, and the mixture was stirred for 4 hours under heat refluxing. The reaction mixture was cooled to room temperature, and n-hexane was added to the reaction mixture. The resulting solid was collected by filtration, washed with a mixture of t-butyl methyl ether and n-hexane, and dried to obtain 180 mg of N-(6-chloro-3-pyridazinyl)-5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide (hereafter, referred to as present compound 17) represented by the formula:

Workup

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

Sources & evidence

ORD record
ord-2c24126f38af41008bd818188b126e93
Source dataset
uspto-grants-2011_05
Patent number
US07943614B2

Reaction notes

Loading…