3,5-Bis(trifluoromethyl)benzoic acid → N-[4-(2-Fluoro-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-3,5-bis-trifluoromethyl-benzamide

HRID 878211Notes

Reaction equation

HRID 878211 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH2:31][CH2:32][S:33]([CH3:36])(=[O:35])=[O:34])[C:15](=[O:30])[C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])N=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=1.F[C:38](F)(F)C1C=C(C=C(C(F)(F)F)C=1)C(O)=O>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH2:31][CH2:32][S:33]([CH3:36])(=[O:35])=[O:34])[C:15](=[O:30])[C:16]1[CH:21]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:38]=[C:18]([C:26]([F:28])([F:29])[F:27])[CH:17]=1

Participants

3

Reactant 2

HCID 128893,5-Bis(trifluoromethyl)benzoic acidHCID 86670772N-[4-(2-Fluoro-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-2,6-bis-trifluoromethyl-isonicotinamide

Product 1

HCID 86670788N-[4-(2-Fluoro-phenyl)-pyridin-3-yl]-N-(2-methanesulfonyl-ethyl)-3,5-bis-trifluoromethyl-benzamideYield 8%

Procedure

The title compound was prepared in analogy to example 90, from [4-(2-fluoro-phenyl)-pyridin-3-yl]-(2-methanesulfonyl-ethyl)-amine (example 159, intermediate) and 3,5-bis(trifluoromethyl)benzoic acid (CAS RN 725-89-3) after a reaction time of 40 hours. The compound was purified by two silica gel chromatographies using a 10 g column and 5 g column, respectively, on a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). The resulting brown solid was suspended in tert-butyl methyl ether, filtered and washed with tert-butyl methyl ether to give the title compound as an off-white solid (8%). MS (ESI): m/z=535.09 [M+H]+.

Workup

  1. customThe compound was purified by two silica gel chromatographies
  2. washrespectively, on a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)
  3. filtrationfiltered
  4. washwashed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-f03b4cd356294129888ae7fdea252a03
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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