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

HRID 381351Notes

Reaction equation

C(N(CC)CC)C.[CH:8]([NH:11][C:12]1[C:13]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([C:26]3[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][N:27]=3)=[O:25])[CH2:20][CH2:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1)([CH3:10])[CH3:9].C(Cl)(=O)C(C)(C)C.[CH2:42]([CH2:44][NH2:45])[OH:43]>C(Cl)Cl>[OH:43][CH2:42][CH2:44][NH:45][C:30]([C:29]1[CH:33]=[CH:34][C:26]([C:24]([N:21]2[CH2:22][CH2:23][N:18]([C:13]3[C:12]([NH:11][CH:8]([CH3:9])[CH3:10])=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:19][CH2:20]2)=[O:25])=[N:27][CH:28]=1)=[O:31]

Participants

Conditions

Temperature: 5 °C

Procedure

Triethylamine (0.54 ml) was added to 6-[1-[3-(isopropylamino)-2-pyridyl]piperazine-4-yl-carbonyl]nicotinic acid (1.3 g) in methylene chloride (40 ml) for dissolution and cooled. With the slow addition of pivaloyl chloride (0.45 ml) at 0° C.˜5° C., the reaction mixture was stirred at 5° C. for 2 hours. With the addition of triethylamine (0.6 ml) and ethanolamine (0.25 ml), the mixture was stirred at 5° C.˜10° C. for 3 hours. The solution was washed with aqueous sodium bicarbonate and water twice. The separated organic layer was concentrated under reduced pressure. The concentrated residue was treated with ether for crystallization and recrystallized with ethanol and isopropyl ether to give a desired compound of 1.2 g (yield: 83%).

Workup

temperaturecooled
stirringthe mixture was stirred at 5° C.˜10° C. for 3 hours
washThe solution was washed with aqueous sodium bicarbonate and water twice
concentrationThe separated organic layer was concentrated under reduced pressure
additionThe concentrated residue was treated with ether for crystallization
customrecrystallized with ethanol and isopropyl ether

Sources & evidence

ORD record: ord-6a51cee20714497890fd21e6b89cb137
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06306860B1

Reaction notes

Loading…