Triethylamine → HCID 58127973, compound

HRID 1257426Notes

Reaction equation

HRID 1257426 reaction equation
[NH:1]([C:3](=[O:15])[CH2:4][N:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[N:6]1)[NH2:2].C(N(CC)CC)C.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29]>ClCCl>[O:15]=[C:3]([NH:1][NH:2][C:28]([C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=1)=[O:29])[CH2:4][N:5]1[CH:9]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[N:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 58127759HCID 58127759, compound

Product 1

HCID 58127973HCID 58127973, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The compound (6.0 g) obtained in Example 123a and triethylamine (8.33 g) were dissolved in dichloromethane (100 mL), and a solution of 3-(trifluoromethyl)benzoylchloride (10.0 g) in dichloromethane (20 ml) was added. The reaction mixture was stirred at room temperature overnight, an insoluble material was removed by filtration, and the filtrate was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether/ethyl acetate/triethylamine=5/1/0.001) to give the title compound (4.1 g) as an oil.

Workup

  1. customan insoluble material was removed by filtration
  2. washthe filtrate was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (carrier: silica gel, eluent: petroleum ether/ethyl acetate/triethylamine=5/1/0.001)

Sources & evidence

ORD record
ord-5b734734c99043d39874c789e3bc5297
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

Loading…