Potassium Carbonate → 1-(5-Cyanopyridin-2-yl)-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamide

HRID 1967742Notes

Reaction equation

HRID 1967742 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]=[C:8]([NH:17][C:18]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[O:19])[S:9][C:10]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.Cl[C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[C:33]([C:30]1[CH:31]=[CH:32][C:27]([N:23]2[CH2:24][CH2:25][CH:20]([C:18]([NH:17][C:8]3[S:9][C:10]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)=[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[N:7]=3)=[O:19])[CH2:21][CH2:22]2)=[N:28][CH:29]=1)#[N:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 23144542N-[4-(2-Furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamide

Product 1

HCID 231444241-(5-Cyanopyridin-2-yl)-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]piperidine-4-carboxamideYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 44 (181 mg, 0.50 mmol), 2-chloro-5-cyanopyridine (104 mg, 0.75 mmol) and potassium carbonate (207 mg, 1.50 mmol) were suspended in 1,4-dioxane (4 mL), followed by stirring overnight under heating and reflux. The insoluble was removed through filtration, the filtrate was distilled away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform:methanol=20:1) to afford the entitled Compound 45 (158 mg, 68%).

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. customThe insoluble was removed through filtration
  4. distillationthe filtrate was distilled away under reduced pressure
  5. customthe resulting residue was purified through silica gel column chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-f082ce9ba73b491fafa7f6482087eb66
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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