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

HRID 1967732Notes

Reaction equation

HRID 1967732 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.[CH2:27]([CH2:29][NH2:30])[OH:28]>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]([NH:30][CH2:29][CH2:27][OH:28])=[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 700EthanolamineHCID 231444172-Chloro-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamide

Product 1

HCID 231444123-Pyridinecarboxamide,n-[4-(2-furanyl)-5-(4-morpholinyl)-2-thiazolyl]-6-[(2-hydroxyethyl)amino]-Yield 59%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 32 (391 mg, 1.00 mmol) was dissolved in 1,4-dioxane (4 mL), and ethanolamine (0.300 mL, 5.00 mmol) was added thereto, followed by stirring overnight under heating and reflux. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of sodium chloride and chloroform were added to the resulting residue, and the precipitated solid was collected by filtration to afford the entitled Compound 33 (244 mg, 59%).

Workup

  1. temperatureunder heating
  2. temperaturereflux
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additiona saturated aqueous solution of sodium chloride and chloroform were added to the resulting residue
  5. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-6fc6bf0cf8344b838c96812f3725a7e9
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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