Methylamine → HCID 58243770, compound

HRID 389150Notes

Reaction equation

HRID 389150 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][C:18]([CH3:36])([C:20]2[N:24]([CH3:25])[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])=[N:22][N:21]=2)[CH3:19])=[C:6]([CH:16]=1)[C:7]([NH:9][CH2:10][C:11](OCC)=[O:12])=[O:8].[CH3:37][NH2:38].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][C:18]([CH3:36])([C:20]2[N:24]([CH3:25])[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:33])([F:34])[F:35])=[N:22][N:21]=2)[CH3:19])=[C:6]([CH:16]=1)[C:7]([NH:9][CH2:10][C:11]([NH:38][CH3:37])=[O:12])=[O:8]

Participants

7

Reactant 4

HCID 6329Methylamine2×HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 58243822HCID 58243822, compound

Product 1

HCID 58243770HCID 58243770, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl N-[5-chloro-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzoyl]glycinate (300 mg) was dissolved in ethanol (6 ml), and methylamine (2.86 ml) was added thereto, followed by stirring at room temperature for one hour. Potassium carbonate (240 mg) was added thereto, followed by stirring at 60° C. for one hour. Methylamine (2.86 ml) was added thereto, followed by stirring at 60° C. for 2 hours. The reaction solution was cooled to room temperature and water and a 1M aqueous sodium hydroxide solution were added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid was washed with diisopropylether to obtain, as a white solid, 5-chloro-N-[2-(methylamino)-2-oxoethyl]-2-(1-methyl-1-{4-methyl-5-[2-(trifluoromethyl)phenyl]-4H-1,2,4-triazol-3-yl}ethoxy)benzamide (131 mg).

Workup

  1. stirringby stirring at 60° C. for one hour
  2. stirringby stirring at 60° C. for 2 hours
  3. temperatureThe reaction solution was cooled to room temperature
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe resulting solid was washed with diisopropylether

Sources & evidence

ORD record
ord-3202a590fd224074aec48937e2b9d4d2
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

Loading…