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

HRID 878164Notes

Reaction equation

HRID 878164 reaction equation
[F:1][CH:2]([F:21])[CH2:3][NH:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[O:19][CH3:20].[F:22][C:23]([F:38])([F:37])[C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[N:32]=1)[C:27](O)=[O:28]>>[F:21][CH:2]([F:1])[CH2:3][N:4]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=1[O:19][CH3:20])[C:27](=[O:28])[C:26]1[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[N:32]=[C:24]([C:23]([F:38])([F:22])[F:37])[CH:25]=1

Participants

3

Reactant 2

HCID 306891352,6-Bis(trifluoromethyl)pyridine-4-carboxylic acidHCID 86670766(2,2-Difluoro-ethyl)-[4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-amine

Product 1

HCID 86670765N-(2,2-Difluoro-ethyl)-N-[4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-2,6-bis-trifluoromethyl-isonicotinamide

Procedure

The title compound was prepared in analogy to example 90, from (2,2-difluoro-ethyl)-[4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-amine and 2,6-bis(trifluoromethyl)isonicotinic acid (Key Organics Ltd.) after a reaction time of 66 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 50:50). Light brown solid (66%). MS (ESI): m/z=542.09 [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 50:50)

Sources & evidence

ORD record
ord-d45c9ca7a4fc4572be83e483764810e7
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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