Trifluoroacetic acid → N-((3-fluoro-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methyl)-5-(piperazin-1-yl)picolinamide

HRID 711259Notes

Reaction equation

HRID 711259 reaction equation
[F:1][C:2]1[C:3]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)=[N:4][CH:5]=[C:6]([CH2:8][NH:9][C:10]([C:12]2[N:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[O:11])[CH:7]=1.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[C:3]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([C:37]([F:40])([F:38])[F:39])[CH:32]=2)=[N:4][CH:5]=[C:6]([CH2:8][NH:9][C:10](=[O:11])[C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:16][N:17]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68079197Tert-butyl 4-(6-((3-fluoro-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methylcarbamoyl)pyridin-3-yl)piperazine-1-carboxylate

Product 1

HCID 68079457N-((3-fluoro-2'-(trifluoromethyl)-2,4'-bipyridin-5-yl)methyl)-5-(piperazin-1-yl)picolinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(6-((3-fluoro-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methylcarbamoyl)pyridin-3-yl)piperazine-1-carboxylate 49-5 (106 mg, 0.21 mmol) in dichloromethane (2 mL) was added TFA (1 mL) dropwise. The mixture was stirred at room temperature for 2 hours, and the solvents were removed by rotary evaporation. The residue was dissolved in ethyl acetate (100 mL), washed with saturated aqueous NaHCO3 solution, H2O and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation to give N-((3-fluoro-2′-(trifluoromethyl)-2,4′-bipyridin-5-yl)methyl)-5-(piperazin-1-yl)picolinamide 49-6 as yellow solid. MS m/z 461.2 (M+1)

Workup

  1. customthe solvents were removed by rotary evaporation
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with saturated aqueous NaHCO3 solution, H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-a6692e020ecd4fcda6339f253b15fc42
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

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