Diglycolamine → 5-[N-[2-(2-hydroxyethoxy)ethyl]carbamoyl]-2-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]pyridine

HRID 381377Notes

Reaction equation

HRID 381377 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][O:32][CH2:33][CH2:34][OH:35]>>[OH:35][CH2:34][CH2:33][O: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

3

Reactant 2

HCID 13578DiglycolamineHCID 109378486-[1-[3-(Isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid methyl ester

Product 1

HCID 98468715-[N-[2-(2-hydroxyethoxy)ethyl]carbamoyl]-2-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]pyridineYield 79%

Procedure

By the same procedure as described in the example 25, the synthesis was carried out starting with 6-[1-[3-(isopropylamino)-2-pyridyl]piperazin-4-yl-carbonyl]nicotinic acid methyl ester and using 2-(2-aminoethoxy)ethanol. And then, the product was recrystallized with acetone and hexane to give a desired compound.

Workup

  1. customAnd then, the product was recrystallized with acetone and hexane

Sources & evidence

ORD record
ord-2594a3c3604d459894fb4545c531e336
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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