Ethanamine, 2,2,2-trifluoro- → HCID 43088331, compound

HRID 655645Notes

Reaction equation

HRID 655645 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:23][C:24]([F:28])([F:27])[CH2:25][NH2:26].[Cl:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([C:36](O)=[O:37])[CH:31]=1>O.ClCCl>[F:23][C:24]([F:28])([F:27])[CH2:25][NH:26][C:36]([C:32]1[CH:31]=[C:30]([Cl:29])[CH:35]=[CH:34][N:33]=1)=[O:37]

Participants

7

Reactant 4

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 757711-HydroxybenzotriazoleHCID 2308904-Chloropyridine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 43088331HCID 43088331, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-hydroxybenzotriazole (0.53 g, 3.5 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSC) (0.67 g, 3.5 mmol) and 2,2,2-trifluoroethyl amine (0.51 ml. 6.35 mmol) were added to a dichloromethane solution (5 ml) of 4-chloropyridine-2-carboxylic acid (0.5 g, 3.17 mmol) and the mixture was stirred at room temperature for one hour. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extraction solution with ethyl acetate was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=11:1→5:1). The purified product was concentrated to dryness under reduced pressure to obtain N-(2,2,2-trifluoroethyl)-4-chloropyridine-2-carboxamide (435 mg) as white powder.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe extraction solution with ethyl acetate was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=11:1→5:1)
  5. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a87b941fcc2b43ecaa4d221019548ab3
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

Loading…