Methylamine → N,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide

HRID 1640695Notes

Reaction equation

HRID 1640695 reaction equation
[CH3:1][C:2]1[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:4](=[O:12])[C:5]([C:8](OC)=[O:9])=[N:6][CH:7]=1.[CH3:23][NH2:24]>>[CH3:23][NH:24][C:8]([C:5]1[C:4](=[O:12])[N:3]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=2)[C:2]([CH3:1])=[CH:7][N:6]=1)=[O:9]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 58432791AZ-32S-methyl-ester

Product 1

HCID 66738835N,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamideYield 73%

Conditions

Temperature
50 °C

Procedure

Methyl 5-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxylate (0.11 g, 0.35 mmol) was dissolved in a solution of methylamine (33% in ethanol, 5 ml) in a vial. The vial was sealed and heated with stirring at 50° C. for 30 minutes. The volatiles were removed in vacuo giving a crude product which was purified for analytical purposes on preparative HPLC to give 0.079 g (73%) of N,5-dimethyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,4-dihydropyrazine-2-carboxamide as a solid.

Workup

  1. customThe vial was sealed
  2. temperatureheated
  3. customThe volatiles were removed in vacuo
  4. customgiving a crude product which
  5. customwas purified for analytical purposes on preparative HPLC

Sources & evidence

ORD record
ord-1806e3ad943347a183ce72c5b3894076
Source dataset
uspto-grants-2012_02
Patent number
US08114881B2

Reaction notes

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