Pyridine → HCID 58696288, compound

HRID 1178334Notes

Reaction equation

HRID 1178334 reaction equation
[C:1]([O:5][C:6](=[O:24])[N:7]([C:9]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)([CH2:13][NH:14][CH3:15])[CH2:10][CH:11]=[CH2:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.ClC(F)(F)C([O:35][C:36](=O)[C:37]([F:40])([F:39])[Cl:38])=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[N:7]([C:9]([CH2:13][N:14]([C:36](=[O:35])[C:37]([Cl:38])([F:40])[F:39])[CH3:15])([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=1)[CH2:10][CH:11]=[CH2:12])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 76074Acetic acid, chlorodifluoro-, anhydrideHCID 516892Sodium BicarbonateHCID 58696296HCID 58696296, compound

Product 1

HCID 58696288HCID 58696288, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl[1-(3,4-dichlorophenyl)-1-methylaminomethyl-3-butenyl]methylcarbamate (500 mg) produced in Example 4 was dissolved in methylene chloride (10 mL). Under cooling with ice, pyridine (163 μL) and chlorodifluoroacetic acid anhydride (350 μL) were added thereto. Under cooling with ice, the mixture was stirred for 50 minutes. Saturated aqueous sodium bicarbonate was added to the reaction mixture, and the resultant mixture was extracted with methylene chloride. The organic layer was washed with saturated brine, dried over sodium sulfate anhydrate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=4:1), to thereby give the title compound (300 mg, 46%).

Workup

  1. additionwere added
  2. temperatureUnder cooling with ice
  3. extractionthe resultant mixture was extracted with methylene chloride
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate anhydrate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-0158647d2a52410983b5da4e75c88e14
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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