Chloroform → N-(6-chloro-3-pyridazinyl)-5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide

HRID 548575Notes

Reaction equation

HRID 548575 reaction equation
[F: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.C(Cl)(Cl)Cl>CO>[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]([F:1])[C:3]=2[OH:16])=[O:13])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 7961BromobenzeneHCID 216436-Amino-3-chloropyridazineHCID 57619577Ethyl 5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 57672125N-(6-chloro-3-pyridazinyl)-5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamideYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

600 mg of ethyl 5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate and 194 mg of 3-amino-6-chloropyridazine were added to 5 ml of bromobenzene, and the mixture was stirred at 160° C. for 4 hours. The reaction mixture was cooled to room temperature, and subjected to silica gel chromatography (chloroform:methanol=20:1). The resulting crude product was washed with a mixture of t-butyl methyl ether and n-hexane, and dried to obtain 311 mg of N-(6-chloro-3-pyridazinyl)-5-fluoro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide (hereinafter, referred to as present compound 19) represented by the formula:

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe resulting crude product was washed with a mixture of t-butyl methyl ether and n-hexane
  3. customdried

Sources & evidence

ORD record
ord-f41b64e9e3134b979aae799e74b15d2e
Source dataset
uspto-grants-2011_05
Patent number
US07943614B2

Reaction notes

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