Triethylamine → HCID 58127830, compound

HRID 1257379Notes

Reaction equation

HRID 1257379 reaction equation
Cl.[NH2:2][CH:3]([C:8]([CH:10]1[CH2:12][CH2:11]1)=[O:9])[C:4]([O:6][CH3:7])=[O:5].[F:13][C:14]([F:25])([F:24])[C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](O)=[O:19].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH:10]1([C:8](=[O:9])[CH:3]([NH:2][C:18]([C:17]2[CH:21]=[CH:22][CH:23]=[C:15]([C:14]([F:13])([F:24])[F:25])[CH:16]=2)=[O:19])[C:4]([O:6][CH3:7])=[O:5])[CH2:12][CH2:11]1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 99633-(Trifluoromethyl)benzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 66939348HCID 66939348, compound

Product 1

HCID 58127830HCID 58127830, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (16 mL) of the compound (3.0 g, 16 mmol) obtained in Example 72a in N,N-dimethylformamide were added 3-trifluoromethylbenzoic acid (3.2 g, 17 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide (3.6 g, 19 mmol), 1-hydroxybenzotriazole (2.9 g, 19 mmol) and triethylamine (4.3 mL, 31 mmol), and the mixture was stirred at room temperature overnight. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give the title compound (4.0 g, 66%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=70/30)

Sources & evidence

ORD record
ord-69f18bd3449845818f6278fcbb093398
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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