2,6-Bis(trifluoromethyl)pyridine-4-carboxylic acid → N-(2,2-Difluoro-ethyl)-N-(2-methoxy-[3,4']bipyridinyl-3'-yl)-2,6-bis-trifluoromethyl-isonicotinamide

HRID 878168Notes

Reaction equation

HRID 878168 reaction equation
[F:1][CH:2]([F:19])[CH2:3][NH:4][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[C:11]1[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=1.[F:20][C:21]([F:36])([F:35])[C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[N:30]=1)[C:25](O)=[O:26]>>[F:19][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[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=1)[C:25](=[O:26])[C:24]1[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[N:30]=[C:22]([C:21]([F:36])([F:20])[F:35])[CH:23]=1

Participants

3

Reactant 2

HCID 306891352,6-Bis(trifluoromethyl)pyridine-4-carboxylic acidHCID 86670768(2,2-Difluoro-ethyl)-(2-methoxy-[3,4]bipyridinyl-3'-yl)-amine

Product 1

HCID 60198030N-(2,2-Difluoro-ethyl)-N-(2-methoxy-[3,4']bipyridinyl-3'-yl)-2,6-bis-trifluoromethyl-isonicotinamide

Procedure

The title compound was prepared in analogy to example 90, from (2,2-difluoro-ethyl)-(2-methoxy-[3,4]bipyridinyl-3′-yl)-amine and 2,6-bis(trifluoromethyl)isonicotinic acid (Key Organics Ltd.) after a reaction time of 67 hours. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:EtOAc (100:0 to 50:50). Light brown solid (64%). MS (ESI): m/z=507.11 [M+H]+.

Workup

  1. customThe compound was purified by silica gel chromatography on a 10 g column
  2. washeluting with a gradient of n-heptane:EtOAc (100:0 to 50:50)

Sources & evidence

ORD record
ord-67e03344ae1646d682c196d1ccf48296
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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