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

HRID 1361765Notes

Reaction equation

HRID 1361765 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-cb5b4f4eef86448685fb46260f2007a5
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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