2,6-Bis(trifluoromethyl)pyridine-4-carboxylic acid → N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-2,6-bis-trifluoromethyl-isonicotinamide

HRID 878150Notes

Reaction equation

HRID 878150 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]([CH3:29])[C:16](=[O:28])[C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])C=C(F)[CH:18]=2)=[C:4]([O:30][CH3:31])[CH:3]=1.[F:32][C:33]([F:48])([F:47])[C:34]1C=C(C=C(C(F)(F)F)[N:42]=1)C(O)=O>>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]([CH3:29])[C:16](=[O:28])[C:17]2[CH:18]=[C:34]([C:33]([F:48])([F:47])[F:32])[N:42]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:22]=2)=[C:4]([O:30][CH3:31])[CH:3]=1

Participants

3

Reactant 2

HCID 306891352,6-Bis(trifluoromethyl)pyridine-4-carboxylic acidHCID 86670751N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-fluoro-N-methyl-5-trifluoromethyl-benzamide

Product 1

HCID 86670756N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-2,6-bis-trifluoromethyl-isonicotinamide

Procedure

The title compound was prepared in analogy to example 90, from [4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine (example 130, intermediate) and 2,6-bis(trifluoromethyl)isonicotinic acid (Key Organics Ltd.) after a reaction time of 23 hours. The compound was purified by silica gel chromatography on a 20 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Light brown solid (38%). MS (ESI): m/z=492.10 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 20 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-e6c829c6ba7842d9b58351b46222a969
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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