Triethylamine → HCID 66654601, compound

HRID 517741Notes

Reaction equation

HRID 517741 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][N:10]=1.[C:19]([O:22][CH2:23][C:24](Cl)=[O:25])(=[O:21])[CH3:20]>C(Cl)Cl>[C:19]([O:22][CH2:23][C:24](=[O:25])[NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:18])[F:17])=[CH:11][N:10]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 66654601HCID 66654601, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (9.30 g, 91.9 mmol) was added at 0° C. to a stirred solution of 2-amino-5-trifluoromethylpyridine (5.0 g, 30.8 mmol) in DCM, and stirring was continued for 15 min. 2-Chloro-2-oxoethyl acetate (5.03 g, 36.8 mmol) was added at 0° C., and the temperature was raised to room temperature and the mixture was stirred for 4 hrs. The reaction mixture was diluted with DCM and washed with ice-water, aq. NaHCO3 solution and saturated brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford the crude compound. This was purified by column chromatography (100-200 silica gel), eluting with 0-20% EtOAc/pet ether to give the title compound (3.30 g) as a pale brown solid.

Workup

  1. stirringthe mixture was stirred for 4 hrs
  2. washwashed with ice-water, aq. NaHCO3 solution and saturated brine solution
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude compound
  6. customThis was purified by column chromatography (100-200 silica gel)
  7. washeluting with 0-20% EtOAc/pet ether

Sources & evidence

ORD record
ord-a693338e6661429987ccd3bbe9fb3fc6
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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