Trifluoroacetic acid → HCID 66878016, compound

HRID 923151Notes

Reaction equation

HRID 923151 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([C:15](=[O:19])[N:16]([CH3:18])[CH3:17])[CH:12]=[CH:11][C:3]=1[C:4]([O:6]C(C)(C)C)=[O:5].C(O)(C(F)(F)F)=O>O>[Cl:1][C:2]1[CH:14]=[C:13]([C:15](=[O:19])[N:16]([CH3:17])[CH3:18])[CH:12]=[CH:11][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66878630HCID 66878630, compound

Product 1

HCID 66878016HCID 66878016, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

290 mg of dimethylamine hydrochloride was coupled to 1 g of 4-(tert-butoxycarbonyl)-3-chlorobenzoic acid via Procedure G. The reaction mixture was diluted with ethyl acetate, washed with 0.1 N HCl, 0.1 N NaOH and brine, dried (MgSO4) and evaporated to afford tert-butyl 2-chloro-4-(dimethylcarbamoyl)benzoate. 1.1 g of tert-butyl 2-chloro-4-(dimethylcarbamoyl)benzoate was treated with TFA (4 mL) containing trace amounts of H2O for 2 h. The reaction mixture was evaporated, and then added 0.1 N HCl. The resulting solid was filtered and washed with H2O to yield 2-chloro-4-(dimethylcarbamoyl)benzoic acid. 100 mg of 4-chloro-3-(pyridine-2-yl)aniline was coupled to 2-chloro-4-(dimethylcarbamoyl)benzoic acid via Procedure G. The product was purified on reverse phase HPLC to yield 2-chloro-N1-(4-chloro-3-(pyridin-2-yl)phenyl)-N4,N4-dimethylterephthalamide. MS (Q1) 414.1 (M)+.

Workup

  1. customThe reaction mixture was evaporated
  2. additionadded 0.1 N HCl
  3. filtrationThe resulting solid was filtered
  4. washwashed with H2O

Sources & evidence

ORD record
ord-72ba71237751410cac995deca3540344
Source dataset
uspto-grants-2016_03
Patent number
US09278961B2

Reaction notes

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