1-Methylpiperazine → 3-Pyridinecarboxamide,n-[4-(2-furanyl)-5-(4-morpholinyl)-2-thiazolyl]-6-(4-methyl-1-piperazinyl)-

HRID 2238700Notes

Reaction equation

HRID 2238700 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.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]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:31]3[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]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 531671-MethylpiperazineHCID 231444172-Chloro-N-[4-(2-furyl)-5-morpholinothiazol-2-yl]pyridine-5-carboxamide

Product 1

HCID 231441133-Pyridinecarboxamide,n-[4-(2-furanyl)-5-(4-morpholinyl)-2-thiazolyl]-6-(4-methyl-1-piperazinyl)-Yield 100%

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 1-methylpiperazine (0.56 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, 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: 28% aqueous ammonia=10:1:1) to afford the entitled Compound 35 (454 mg, 100%).

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: 28% aqueous ammonia=10:1:1)

Sources & evidence

ORD record
ord-287affb600294161b8a1b2fa80afa00b
Source dataset
uspto-grants-2010_05
Patent number
US07718808B2

Reaction notes

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