Water → HCID 53829439, compound

HRID 582317Notes

Reaction equation

HRID 582317 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.[CH3:29][O:30][CH2:31][CH2:32][NH2:33].O>CO>[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:33][CH2:32][CH2:31][O:30][CH3:29])=[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

5

Reactant 3

HCID 962WaterHCID 80182-MethoxyethylamineHCID 53711670HCID 53711670, compound

Product 1

HCID 53829439HCID 53829439, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid methyl ester (1.6 g) was dissolved in methanol (35 ml) and then, 2-methoxyethylamine (0.68 g) was added. And then, the reaction mixture was heated to reflux for 10 hours. The mixture was cooled, and after excess of water was added slowly to the solution at 35~40° C. to precipitate the crystals, the solution was slowly cooled again, stirred at 10° C. for 1 hour and filtered. The filtered solid was washed with a co-solvent (water:methanol=4:1, v/v) and was recrystallized using isopropanol and ether, filtered and dried to give 1.39 g (yield: 78%) of the desired compound. m.p.: 120~121° C.; 1H-NMR(CDCl3), ppm: δ 1.23(d, 6H), 3.15(m, 4H), 3.38(s, 3H), 3.55(m, 5H), 3.64(m, 2H), 3.91(m, 2H), 6.55(m, 1H), 6.90(m, 1H), 6.99(m, 1H), 7.49(m, 2H), 7.70(m, 1H), 7.81(m, 2H)

Workup

  1. temperatureAnd then, the reaction mixture was heated
  2. temperatureto reflux for 10 hours
  3. temperatureThe mixture was cooled
  4. customto precipitate the crystals
  5. temperaturethe solution was slowly cooled again
  6. filtrationfiltered
  7. washThe filtered solid was washed with a co-solvent (water
  8. custommethanol=4:1, v/v) and was recrystallized
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-c6ce4b115d2d4f4480e6ca71b77dd25b
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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