6-[4-(3-BENZYL-5-TRIFLUOROMETHYL-3H-[1,2,3]TRIAZOLE-4-CARBONYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (3-METHYLBUTYL)AMIDE → 6-[4-(5-trifluoromethyl-3H-[1,2,3]triazole-4-carbonyl)-piperazin-1-yl]pyridazine-3-carboxylic acid (3-methylbutyl)amide

HRID 2354741Notes

Reaction equation

HRID 2354741 reaction equation
[CH3:1][CH:2]([CH3:38])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([C:22]3[N:23](CC4C=CC=CC=4)[N:24]=[N:25][C:26]=3[C:27]([F:30])([F:29])[F:28])=[O:21])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1)=[O:7]>CO.C(O)(=O)C.[Pd]>[CH3:1][CH:2]([CH3:38])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[N:9]=[N:10][C:11]([N:14]2[CH2:15][CH2:16][N:17]([C:20]([C:22]3[NH:23][N:24]=[N:25][C:26]=3[C:27]([F:29])([F:28])[F:30])=[O:21])[CH2:18][CH2:19]2)=[CH:12][CH:13]=1)=[O:7]

Participants

5

Reactant 1

HCID 668495356-[4-(3-BENZYL-5-TRIFLUOROMETHYL-3H-[1,2,3]TRIAZOLE-4-CARBONYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (3-METHYLBUTYL)AMIDE

Product 1

HCID 1784464906-[4-(5-trifluoromethyl-3H-[1,2,3]triazole-4-carbonyl)-piperazin-1-yl]pyridazine-3-carboxylic acid (3-methylbutyl)amideYield 36.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6-[4-(3-Benzyl-5-trifluoromethyl-3H-[1,2,3]triazole-4-carbonyl)piperazin-1-yl]pyridazine-3-carboxylic acid (3-methylbutyl)amide (0.4 g, 0.75 mmol) was dissolved in 10 mL of MeOH with 3 drops of acetic acid and 0.2 g of 10% Pd/C was added. The reaction mixture was kept under normal pressure of H2 at ambient temperature overnight. After filtration the reaction mixture was evaporated under reduced pressure and the residue was recrystallized from 3 mL of EtOH to give 120 mg (36% yield) of 6-[4-(5-trifluoromethyl-3H-[1,2,3]triazole-4-carbonyl)-piperazin-1-yl]pyridazine-3-carboxylic acid (3-methylbutyl)amide as a white powder. 1H NMR (500 MHz, Acetone-d6) δ 8.18, 7.91, 7.32, 3.92-3.72, 3.45, 1.67, 1.52, 0.92.

Workup

  1. additionwas added
  2. filtrationAfter filtration the reaction mixture
  3. customwas evaporated under reduced pressure
  4. customthe residue was recrystallized from 3 mL of EtOH

Sources & evidence

ORD record
ord-eff805a74e6f4dffa1abc301ace6148d
Source dataset
uspto-grants-2010_07
Patent number
US07754711B2

Reaction notes

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