Methylamine → N-methyl-2-(trifluoromethoxy)-5-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzamide

HRID 406436Notes

Reaction equation

HRID 406436 reaction equation
C(O[C:4](=[O:17])[C:5]1[CH:10]=[C:9](Br)[CH:8]=[CH:7][C:6]=1[O:12][C:13]([F:16])([F:15])[F:14])C.[CH3:18][NH2:19].[F:20][C:21]([F:35])([F:34])[C:22]1[N:26]2[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][C:25]2=[N:24][N:23]=1>>[CH3:18][NH:19][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:28]2[CH:29]=[CH:30][C:25]3[N:26]([C:22]([C:21]([F:35])([F:34])[F:20])=[N:23][N:24]=3)[CH:27]=2)[CH:8]=[CH:7][C:6]=1[O:12][C:13]([F:14])([F:15])[F:16]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 44829039Ethyl 5-bromo-2-(trifluoromethoxy)benzoateHCID 581189153-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-ylboronic acid

Product 1

HCID 86650231N-methyl-2-(trifluoromethoxy)-5-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzamide

Procedure

In a heavy-wall pressure tube was added ethyl-5-bromo-2-(trifluoromethoxy)benzoate (0.3 mL) and methylamine (1.5 mL). The mixture was heated at 60 C for 2 hours. The reaction mixture was concentrated to afford A which was coupled to with 3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-ylboronic acid using methods disclosed above to give to give N-methyl-2-(trifluoromethoxy)-5-[3-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridin-6-yl]benzamide.

Workup

  1. temperatureThe mixture was heated at 60 C for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. customto afford A which
  4. customto give

Sources & evidence

ORD record
ord-6943c1a982a24d59b931d1af44505131
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

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