4-Fluorobenzoyl chloride → HCID 22266494, compound

HRID 489293Notes

Reaction equation

HRID 489293 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[N:4]([CH2:10][CH2:11][CH2:12][CH3:13])[C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=1.[F:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1>N1C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[CH2:10]([N:4]1[C:5]([CH3:9])=[C:6]([CH3:8])[CH:7]=[C:2]([NH:1][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][C:16]([F:15])=[CH:17][CH:18]=2)[C:3]1=[O:14])[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 22266463HCID 22266463, compound

Product 1

HCID 22266494HCID 22266494, compoundYield 54.2%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Amino-1-butyl-5,6-dimethyl-2-pyridone (5-004-02) (117 mg) was dissolved in pyridine (1 mL), and the reaction mixture was stirred under ice-cooling and nitrogen atmosphere, and to the reaction mixture was added dropwise a solution of 4-fluorobenzoyl chloride (0.08 mL) in tetrahydrofuran (1 mL) over 10 min, followed by stirring at the same condition. After 3 h, the reaction mixture was diluted with ethyl acetate and poured into ice-water, extracted once with ethyl acetate, washed with aqueous hydrochloric acid solution, water, an aqueous solution of sodium bicarbonate, and water, dried over magnesium sulfate, and evaporated under reduced pressure. The obtained crystal residue (202 mg) was recrystallized from methylene chloride/n-hexane to give 1-butyl-3-(4-fluorobenzoyl)amino-5,6-dimethyl-2-pyridone (5-004) (103 mg, 54.2%, m.p. 129 to 130° C.) as a colorless needle.

Workup

  1. temperaturecooling
  2. stirringby stirring at the same condition
  3. extractionextracted once with ethyl acetate
  4. washwashed with aqueous hydrochloric acid solution, water
  5. dry with materialan aqueous solution of sodium bicarbonate, and water, dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe obtained crystal residue (202 mg) was recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-a6cdae04b0d5487cb41bde80b51a69b0
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

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