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

HRID 878176Notes

Reaction equation

HRID 878176 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[C:15]([O:20][CH3:21])=[N:16][CH:17]=[CH:18][CH:19]=1)(=[O:4])=[O:3].[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]>>[CH3:1][S:2]([CH2:5][CH2:6][N:7]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[C:15]([O:20][CH3:21])=[N:16][CH:17]=[CH:18][CH:19]=1)[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)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 306891352,6-Bis(trifluoromethyl)pyridine-4-carboxylic acidHCID 70663393(2-Methanesulfonyl-ethyl)-(2-methoxy-[3,4']bipyridinyl-3'-yl)-amine

Product 1

HCID 60196488N-(2-Methanesulfonyl-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-methanesulfonyl-ethyl)-(2-methoxy-[3,4]bipyridinyl-3′-yl)-amine and 2,6-bis(trifluoromethyl) isonicotinic acid (Key Organics Ltd.) after a reaction time of 15 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 0:100). Light brown solid (14%). MS (ESI): m/z=549.10 [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 0:100)

Sources & evidence

ORD record
ord-6df72886713740a990d8bcc80362bd62
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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