N-methyl-4-o-tolylpyridin-3-amine → 3-Cyano-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethyl-benzamide

HRID 878155Notes

Reaction equation

HRID 878155 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].[C:16]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:21]([OH:23])=O)#[N:17]>>[C:16]([C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:21]([N:2]([CH3:1])[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:23])#[N:17]

Participants

3

Reactant 2

HCID 18403336N-methyl-4-o-tolylpyridin-3-amineHCID 589022873-Cyano-5-(trifluoromethyl)benzoic acid

Product 1

HCID 706635343-Cyano-N-methyl-N-(4-o-tolyl-pyridin-3-yl)-5-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 90, from N-methyl-4-o-tolylpyridin-3-amine (example 1, intermediate a) and 3-cyano-5-trifluoromethyl-benzoic acid after a reaction time of 94 hours. The product was purified by silica gel chromatography using a 10 g column eluting with EtOAc followed by a second chromatography on a 5 g column eluting with a gradient of n-heptane:EtOAc (100:0 to 50:50). Colorless solid (2%). MS (ESI): m/z=396.13 [M+H]+.

Workup

  1. customThe product was purified by silica gel chromatography
  2. washeluting with EtOAc
  3. washeluting with a gradient of n-heptane:EtOAc (100:0 to 50:50)

Sources & evidence

ORD record
ord-ff244806944042c8ba950434dce90d76
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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