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

HRID 381362Notes

Reaction equation

HRID 381362 reaction equation
[NH2:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=3)=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[CH2:50]([CH2:52][NH2:53])[OH:51]>C(Cl)Cl.O1CCCC1>[NH2:1][C:2]1[C:3]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:24]=[CH:23][C:19]([C:20](=[O:21])[NH:53][CH2:52][CH2:50][OH:51])=[CH:18][N:17]=3)=[O:15])[CH2:10][CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 700EthanolamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 183627906-[1-(3-Amino-2-pyridyl)piperazin-4-yl-carbonyl]nicotinic acid

Product 1

HCID 4997296-[4-(3-amino-2-pyridyl)piperazine-1-carbonyl]-N-(2-hydroxyethyl)pyridine-3-carboxamideYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

6-[1-(3-Amino-2-pyridyl)piperazine-4-yl-carbonyl]nicotinic acid (0.5 g) was added to a co-solvent of tetrahydrofuran (10 ml) and methylene chloride (10 ml) and with the successive addition of 1,3-dicyclohexylcarbodimide (0.65 g) and 1-hydroxybenzotriazole (0.23 g) at 15˜20° C., the mixture was stirred for 2 hours. With the addition of ethanolamine (0.18 ml), the mixture was stirred again at 20˜25° C. for 2 hours. Methylene chloride (30 ml) was added again to the mixture, washed with water 3 times, dried over magnesium sulfate and concentrated under reduced pressure. The concentrated residue was treated with ether for crystallization. The solid was recrystallized with ethanol and hexane to give a desired compound of 0.44 g (yield: 78%).

Workup

  1. stirringthe mixture was stirred again at 20˜25° C. for 2 hours
  2. washwashed with water 3 times
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionThe concentrated residue was treated with ether for crystallization
  6. customThe solid was recrystallized with ethanol and hexane

Sources & evidence

ORD record
ord-231f87ab9010466d802dbba06279a088
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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