Water → N-(3-hydroxypropyl)-6-[4-[3-(isopropylamino)-2-pyridyl]piperazine-1-carbonyl]pyridine-3-carboxamide

HRID 381352Notes

Reaction equation

HRID 381352 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])=[N:6][CH:5]=1.[NH2:29][CH2:30][CH2:31][CH2:32][OH:33].O>CO>[OH:33][CH2:32][CH2:31][CH2:30][NH:29][C:3]([C:4]1[CH:9]=[CH:8][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])=[N:6][CH:5]=1)=[O:28]

Participants

5

Reactant 3

HCID 962WaterHCID 90863-Amino-1-propanolHCID 109378486-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid methyl ester

Product 1

HCID 499740N-(3-hydroxypropyl)-6-[4-[3-(isopropylamino)-2-pyridyl]piperazine-1-carbonyl]pyridine-3-carboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-[1-[3-(Isopropylamino)-2-pyridyl]piperazine-4-yl-carbonyl]nicotinic acid methyl ester (2.5 g) was dissolved in methanol (40 ml) and with the addition of 3-amino-1-propanol (0.95 g), the mixture was heated to reflux for 12 hours and cooled. The excess of water was added slowly at 25° C. for precipitation, the mixture was stirred for 2 hours and filtered. The filtered solid was recrystallized with isopropanol and ether, filtered and dried to give a desired compound of 2.17 g (yield: 78%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 12 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtered solid was recrystallized with isopropanol and ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-3fec5f37eb44411584295af90c1ecc64
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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