Water → HCID 54547942, compound

HRID 582320Notes

Reaction equation

HRID 582320 reaction equation
CO[C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[C:23]([NH:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:14][CH2:13]2)=[O:11])=[CH:6][CH:5]=1.[NH2:29][CH2:30][CH2:31][N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.O>C(O)C.C(#N)C>[CH:25]([NH:24][C:23]1[C:18]([N:15]2[CH2:16][CH2:17][N:12]([C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3](=[O:28])[NH:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:5][CH:6]=3)=[O:11])[CH2:13][CH2:14]2)=[N:19][CH:20]=[CH:21][CH:22]=1)([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 962WaterHCID 4082852-MorpholinoethylamineHCID 53711670HCID 53711670, compound

Product 1

HCID 54547942HCID 54547942, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid methyl ester (1.2 g) was dissolved in a co-solvent of ethanol (10 ml) and acetonitrile (20 ml), and 4-(2-aminoethyl)morpholine (0.82 g) was added. The reaction mixture was heated to reflux for 15 hours and cooled. After excess of water was added to the solution at 30° C. to precipitate the crystals, the solution was stirred for 1 hour. Then, the solution was again cooled slowly, stirred at 10~15° C. for 2 hours and filtered. The filtered crystal was washed with preheated water(40° C.) and was recrystallized using isopropanol and ether, filtered and dried to give 1.22 g (yield: 81%) of the desired compound.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 15 hours
  4. temperaturecooled
  5. customto precipitate the crystals
  6. temperatureThen, the solution was again cooled slowly
  7. stirringstirred at 10~15° C. for 2 hours
  8. filtrationfiltered
  9. washThe filtered crystal was washed with preheated water(40° C.)
  10. customwas recrystallized
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-d9ba63fa0b444ce299a0bfb70e6c7b93
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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