4-Aminopyridine → (4Z,7Z,10Z,13Z,16Z,19Z)-N-(Pyridin-4-yl)docosa-4,7,10,13,16,19-hexaenamide

HRID 1631817Notes

Reaction equation

HRID 1631817 reaction equation
[C:1]([OH:24])(=O)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[NH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.C1CCC(N=C=NC2CCCCC2)CC1>>[N:29]1[CH:30]=[CH:31][C:26]([NH:25][C:1](=[O:24])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6]/[CH:7]=[CH:8]\[CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH3:22])=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 17274-AminopyridineHCID 10868DicyclohexylcarbodiimideHCID 175542Docosahexenoic acid

Product 1

HCID 59539431(4Z,7Z,10Z,13Z,16Z,19Z)-N-(Pyridin-4-yl)docosa-4,7,10,13,16,19-hexaenamideYield 91%

Procedure

Reaction of docosahexaenoic acid (0.10 g, 0.30 mmol) with 4-aminopyridine (0.03 g, 0.30 mmol) was conducted according to the general amide coupling procedure using DCC to obtain the product as a yellow solid (0.11 g, 91%). EIMS m/z: 405 ([M]+).

Sources & evidence

ORD record
ord-d2c987f85cc0431eb99d2e24c827e201
Source dataset
uspto-grants-2014_07
Patent number
US08791275B2

Reaction notes

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