Diethylamine → HCID 86625524, compound

HRID 2265956Notes

Reaction equation

HRID 2265956 reaction equation
Cl[C:2]1[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5].[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:18]([N:20]([CH2:21][CH3:22])[C:2]1[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:3]=1[C:4]([N:6]([O:8][CH3:9])[CH3:7])=[O:5])[CH3:19]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 11430Potassium CarbonateHCID 59598164HCID 59598164, compound

Product 1

HCID 86625524HCID 86625524, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 2-chloro-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (400 mg, 1.489 mmol) and diethylamine (0.773 ml, 7.44 mmol) in DMF (4 ml) was added K2CO3 (1.02 g, 7.44 mmol). The mixture was stirred for 4 hours at 110° C. The reaction mixture was diluted with EtOAc (30 ml) and then washed two times with 1N-HCl (30 ml) and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was chromatographed to yield the 2-diethylamino-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (400 mg, 88%).

Workup

  1. washwashed two times with 1N-HCl (30 ml) and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was chromatographed

Sources & evidence

ORD record
ord-04320c6ea708497ea1b9cf65aac2d64b
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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