4-Aminopyridine → (2z,4e,6e,8e)-3,7-Dimethyl-n-(pyridin-4-yl)-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenamide

HRID 1631816Notes

Reaction equation

HRID 1631816 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]\[C:18]([OH:20])=O.[NH2:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH3:21]/[C:16](/[CH:15]=[CH:14]/[CH:13]=[C:12](\[CH3:22])/[CH:11]=[CH:10]/[C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])=[CH:17]/[C:18]([NH:23][C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=[O:20]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 10868DicyclohexylcarbodiimideHCID 5282379Isotretinoin

Product 1

HCID 59539419(2z,4e,6e,8e)-3,7-Dimethyl-n-(pyridin-4-yl)-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenamideYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 13-cis-retinoic acid (0.10 g, 0.33 mmol), CH2Cl2 (5 mL), 4-aminopyridine (0.03 g, 0.33 mmol), and DCC (0.07 g, 0.33 mmol) was stirred at room temperature for 24 h. The mixture was filtered, concentrated, and purified by silica gel flash column chromatography to give the product as a yellow solid (0.07 g, 57%). EIMS m/z: 377 ([M]+), 375 ([M]−).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-ac48fceb2fa14eff8bbb256f5f830ca2
Source dataset
uspto-grants-2014_07
Patent number
US08791275B2

Reaction notes

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