Water → HCID 57242715, compound

HRID 582310Notes

Reaction equation

HRID 582310 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][C@@H:30]([CH3:33])[CH2:31][OH:32].O>CO>[OH:32][CH2:31][C@@H:30]([NH:29][C:3]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]3[C:23]([NH:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:21]=[CH:20][N:19]=3)[CH2:16][CH2:17]2)=[O:11])=[CH:8][CH:9]=1)=[O:28])[CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 80307L-AlaninolHCID 53711670HCID 53711670, compound

Product 1

HCID 57242715HCID 57242715, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

4-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]benzoic acid methyl ester (1.8 g) and (S)-(+)-2-amino-1-propanol (0.71 g) were dissolved in methanol (30 ml) and heated to reflux for 12 hours. The reaction mixture was cooled and with the slow addition of excess of water at 40° C. to precipitate the crystals, the mixture was cooled again and stirred at 20° C. for 1 hour. Following with filtration and washing with water, the filtered solid was recrystallized using isopropanol and ether, filtered and dried to give 1.66 g (yield: 83%) of the desired compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. customto precipitate the crystals
  4. temperaturethe mixture was cooled again
  5. filtrationFollowing with filtration
  6. washwashing with water
  7. customthe filtered solid was recrystallized
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-e9ef6aa66ec2452984bcda37ffe9fc41
Source dataset
uspto-grants-1999_07
Patent number
US05922871

Reaction notes

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