Potassium Carbonate → N-(2-Cyclopropylethyl)-6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxamide

HRID 1714860Notes

Reaction equation

HRID 1714860 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([NH:10][CH2:11][CH2:12][CH:13]2[CH2:15][CH2:14]2)=[O:9])=[CH:4][CH:3]=1.[F:16][C:17]([F:32])([F:31])[C:18]1[CH:30]=[CH:29][CH:28]=[CH:27][C:19]=1[O:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1.CCOC(C)=O>[CH:13]1([CH2:12][CH2:11][NH:10][C:8]([C:5]2[N:6]=[N:7][C:2]([N:24]3[CH2:23][CH2:22][CH:21]([O:20][C:19]4[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=4[C:17]([F:16])([F:31])[F:32])[CH2:26][CH2:25]3)=[CH:3][CH:4]=2)=[O:9])[CH2:15][CH2:14]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 50187904-[2-(Trifluoromethyl)phenoxy]piperidineHCID 655615656-Chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide

Product 1

HCID 11590143N-(2-Cyclopropylethyl)-6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine-3-carboxamide

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-chloro-N-(2-cyclopropylethyl)pyridazine-3-carboxamide (180 mg, 0.73 mmol), 4-[2-(trifluoromethyl)phenoxy]piperidine (150 mg, 0.67 mmol), potassium carbonate (184 mg, 1.33 mmol) and tetrabutylammonium iodide (7 mg, 0.02 mmol) in dioxane (10 mL) was refluxed for 2 days. After cooling, the mixture was diluted with EtOAc and filtered through celite. Solvent was removed in vacuo. Combi-Flash chromatography (10 g, 50-80% EtOAc in hexanes in 20 min, 20 mL/min, 18 mL/fraction) gave the title compound as a white powder. 1H NMR (500 MHz, acetone-d6): δ 0.11-0.13 (m, 2H), 0.45-0.49 (m, 2H), 0.76-0.84 (m, 1H), 1.56 (q, 2H), 2.13-2.20 (m, 4H), 3.52-3.56 (m, 2H), 3.91-3.97 (m, 2H), 4.00-4.06 (m, 2H), 5.01-5.05 (m, 1H), 7.12 (t, 1H), 7.37 (m, 2H), 7.61-7.67 (m, 2H), 7.92 (d, 1H), 8.24 (s, 1H); MS (+ESI) m/z 435 (MH+).

Workup

  1. temperaturewas refluxed for 2 days
  2. temperatureAfter cooling
  3. filtrationfiltered through celite
  4. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-4946a0f056fb4037ac545aa1ce1317dd
Source dataset
uspto-grants-2010_09
Patent number
US07799787B2

Reaction notes

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