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 1631816

Reaktionsgleichung

Reaktionsgleichung von HRID 1631816
[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]

Komponenten

5

Edukt 3

HCID 17274-AminopyridineHCID 10868DicyclohexylcarbodiimideHCID 5282379Isotretinoin

Produkt 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-tetraenamideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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]−).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ac48fceb2fa14eff8bbb256f5f830ca2
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791275B2

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