Triethylamine → HCID 53493384, compound

HRID 1854812Notes

Reaction equation

HRID 1854812 reaction equation
[N:1]1([C:7]2[N:8]=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:20][C:21]([C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27])([F:23])[F:22].CCOC(C)=O>C(Cl)Cl>[N:9]1[CH:10]=[CH:11][N:12]=[C:7]([N:1]2[CH2:6][CH2:5][N:4]([C:26]([C:25]3[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=3[C:21]([F:20])([F:22])[F:23])=[O:27])[CH2:3][CH2:2]2)[N:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 12296696HCID 12296696, compound

Product 1

HCID 53493384HCID 53493384, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 3 is prepared according to synthesis method 2: 0.4 g (2.42 mmoles) of derivative 5a is placed in 10 ml of CH2Cl2. 0.5 ml (3.63 mmoles) of triethylamine is added. At 0° C., 0.4 ml (2.66 mmoles) of trifluoromethylbenzoyl chloride is added drop by drop, the reaction medium is stirred at ambient temperature for 18 hours. After concentrating the reaction medium to dryness, the residue obtained is taken up with AcOEt and washed with water. After drying on MgSO4, the organic phase is concentrated. The residue obtained is purified by silica flash chromatography (CH2Cl2,100%). 0.72 g of yellow powder is isolated (yield: 95%).

Workup

  1. customaccording to synthesis method 2
  2. concentrationAfter concentrating the reaction medium to dryness
  3. customthe residue obtained
  4. washwashed with water
  5. customAfter drying on MgSO4
  6. concentrationthe organic phase is concentrated
  7. customThe residue obtained
  8. customis purified by silica flash chromatography (CH2Cl2,100%)

Sources & evidence

ORD record
ord-442549949af141279dab38c84a19b011
Source dataset
uspto-grants-2015_02
Patent number
US08962837B2

Reaction notes

Loading…