Morpholine → 3-Pyridinecarboxamide,n-[4-(2-furanyl)-5-(4-morpholinyl)-2-thiazolyl]-6-(4-morpholinyl)-

HRID 2238699Notes

Reaction equation

HRID 2238699 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[S:12][C:13]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[C:14]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[O:9])=[CH:4][N:3]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>O1CCOCC1>[O:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:14]1[N:15]=[C:11]([NH:10][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[N:3][CH:4]=2)=[O:9])[S:12][C:13]=1[N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 231444172-Chloro-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamide

Product 1

HCID 231447793-Pyridinecarboxamide,n-[4-(2-furanyl)-5-(4-morpholinyl)-2-thiazolyl]-6-(4-morpholinyl)-Yield 84.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 32 (391 mg, 1.00 mmol) was dissolved in 1,4-dioxane (10 mL), and morpholine (0.44 mL, 5.00 mmol) was added thereto, followed by stirring under heating and reflux for 10 hours. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of sodium chloride was added to the resulting residue, followed by extraction with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=19:1) to afford the entitled Compound 34 (372 mg, 84%).

Workup

  1. temperatureunder heating
  2. temperaturereflux for 10 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiona saturated aqueous solution of sodium chloride was added to the resulting residue
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled away under reduced pressure
  9. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-b05220a5c3af429f9bcb375670e620ea
Source dataset
uspto-grants-2010_05
Patent number
US07718808B2

Reaction notes

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