Potassium Hydroxide → 5-(3-(Aminomethyl)-2,6-dimethylphenyl)-2-(4-(trifluoromethyl)phenyl)-2H-1,2,4-triazol-3(4H)-one

HRID 59356Notes

Reaction equation

HRID 59356 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[NH:12][C:11]([C:15]3[C:16]([CH3:30])=[C:17]([CH:26]=[CH:27][C:28]=3[CH3:29])[CH2:18][NH:19]C(=O)C(F)(F)F)=[N:10]2)=[CH:5][CH:4]=1.[OH-].[K+]>C1COCC1>[NH2:19][CH2:18][C:17]1[C:16]([CH3:30])=[C:15]([C:11]2[NH:12][C:13](=[O:14])[N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:31])([F:32])[F:1])=[CH:4][CH:5]=3)[N:10]=2)[C:28]([CH3:29])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 136246060N-(3-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2,4-dimethylbenzyl)-2,2,2-trifluoro acetamide

Product 1

HCID 1364924295-(3-(Aminomethyl)-2,6-dimethylphenyl)-2-(4-(trifluoromethyl)phenyl)-2H-1,2,4-triazol-3(4H)-oneYield 31.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-(1-(4-(trifluoromethyl)phenyl)-4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-2,4-dimethylbenzyl)-2,2,2-trifluoro acetamide (Example-106, 0.800 g, 1.74 mmol) in THF (10 mL), aqueous solution of KOH was added and the reaction mass was stirred at RT for 3-4 h. After completion of the reaction, the reaction mass was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.200 g of the desired product. MS (m/z): 362.86 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mass was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e922a3dc1d29414c949fc8e3ddd84471
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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