Potassium Carbonate → 6-{4-[Methyl(2-trifluoromethylphenyl)amino]piperidin-1-YL}pyridazine-3-carboxylic acid (2-cyclopropylethyl)amide

HRID 552171Notes

Reaction equation

HRID 552171 reaction equation
[CH3:1][N:2]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[CH:19]1([CH2:22][CH2:23][NH:24][C:25]([C:27]2[N:28]=[N:29][C:30](Cl)=[CH:31][CH:32]=2)=[O:26])[CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].O1CCOCC1>[CH:19]1([CH2:22][CH2:23][NH:24][C:25]([C:27]2[N:28]=[N:29][C:30]([N:16]3[CH2:17][CH2:18][CH:13]([N:2]([CH3:1])[C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[C:9]([F:12])([F:11])[F:10])[CH2:14][CH2:15]3)=[CH:31][CH:32]=2)=[O:26])[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 578744214-Piperidinamine, N-methyl-N-[2-(trifluoromethyl)phenyl]-HCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Product 1

HCID 117120206-{4-[Methyl(2-trifluoromethylphenyl)amino]piperidin-1-YL}pyridazine-3-carboxylic acid (2-cyclopropylethyl)amideYield 60%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methylpiperidin-4-yl-(2-trifluoromethylphenyl)amine (0.130 g, 0.500 mmol), 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide (0.113 g, 0.500 mmol), K2CO3 (0.100 g, 0.720 mmol) and n-Bu4NI (10 mg) in dioxane (10 mL) was heated to reflux overnight, then concentrated and purified by column chromatography to afford the title compound in 60% yield (0.147 g). 1H NMR (300 MHz, CDCl3) δ 8.30-8.26 (m, 1H), 8.10-7.95 (m, 1H), 7.64 (d, J=7.8 Hz, 1H), 7.55-7.34 (m, 2H), 7.28 (d, J=7.8 Hz, 1H), 4.51 (s, br, 2H), 3.83-3.28 (m, 5H), 2.67 (s, 3H), 2.07-1.98 (m, 2H), 1.77 (s, br, 2H), 1.51-1.44 (m, 2H), 0.68-0.66 (m, 1H), 0.47-0.38 (m, 2H), 0.07-0.03 (m, 2H). MS (ES+) m/z 448.4 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-4cc89a65a1b74b569bef3e8cfba27318
Source dataset
uspto-grants-2011_05
Patent number
US07951805B2

Reaction notes

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