Trifluoroacetic acid → N-((3-fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methyl)-6-(piperazin-1-yl)nicotinamide

HRID 711252Notes

Reaction equation

HRID 711252 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[CH:13]=[CH:14][C:15]([N:18]3[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]3)=[N:16][CH:17]=2)=[O:11])[CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[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)=[N:16][CH:17]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86679720Tert-butyl 4-(5-(((3-fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methyl)carbamoyl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 67208681N-((3-fluoro-2'-(trifluoromethyl)-[2,4'-bipyridin]-5-yl)methyl)-6-(piperazin-1-yl)nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the tert-butyl 4-(5-(((3-fluoro-2′-(trifluoromethyl)-[2,4′-bipyridin]-5-yl)methyl)carbamoyl)pyridin-2-yl)piperazine-1-carboxylate 46-2 in DCM (3.0 mL) was added trifluoroacetic acid (1.0 mL) and the solution was stirred overnight. The reaction mixture was concentrated, redistributed between ethyl acetate and 5% Na2CO3 solution and the organic phase dried over Na2SO4. Concentration with rotavap gave crude N-((3-fluoro-2′-(trifluoromethyl)-[2,4′-bipyridin]-5-yl)methyl)-6-(piperazin-1-yl)nicotinamide 46-3.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dry with materialthe organic phase dried over Na2SO4
  3. concentrationConcentration with rotavap

Sources & evidence

ORD record
ord-b5bb780496234855b5735cfc2d7a4cd7
Source dataset
uspto-grants-2015_11
Patent number
US09181235B2

Reaction notes

Loading…