4-(3-(2-chloro-5-((2,2,2-trifluoroacetamido)methyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(difluoromethyl)phenyl)-2-methoxybenzamide → 4-(3-(5-(aminomethyl)-2-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(difluoromethyl)phenyl)-2-methoxybenzamide

HRID 508789Notes

Reaction equation

HRID 508789 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9]C(=O)C(F)(F)F)=[CH:4][C:3]=1[C:16]1[NH:20][C:19](=[O:21])[N:18]([C:22]2[CH:39]=[CH:38][C:25]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([F:37])[F:36])[CH:30]=3)=[O:27])=[C:24]([O:40][CH3:41])[CH:23]=2)[N:17]=1>[OH-].[K+].N>[NH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:16]2[NH:20][C:19](=[O:21])[N:18]([C:22]3[CH:39]=[CH:38][C:25]([C:26]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]([F:37])[F:36])[CH:30]=4)=[O:27])=[C:24]([O:40][CH3:41])[CH:23]=3)[N:17]=2)[CH:4]=1

Participants

4

Reactant 1

HCID 1364924074-(3-(2-chloro-5-((2,2,2-trifluoroacetamido)methyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(difluoromethyl)phenyl)-2-methoxybenzamide

Product 1

HCID 1366125144-(3-(5-(aminomethyl)-2-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(difluoromethyl)phenyl)-2-methoxybenzamideYield 27.3%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 14797Potassium HydroxideSolvent

Procedure

The solution of 4-(3-(2-chloro-5-((2,2,2-trifluoroacetamido)methyl)phenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-N-(3-(difluoromethyl)phenyl)-2-methoxybenzamide (0.070 g, 0.11 mmol) in 20% aq. KOH (10 mL) and aq. NH3 (2 mL) was stirred for 24 h at RT. Excess of solvent was removed under vacuum and filtered off to afford 0.015 g of desired product.

Workup

  1. customExcess of solvent was removed under vacuum
  2. filtrationfiltered off

Sources & evidence

ORD record
ord-62afff310db54652855a49a7620e5ec3
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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