Ethyl Acetate → N-(6-chloro-4-methyl-9H-beta-carbolin-8-yl)-nicotinamide

HRID 552223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552223
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:15])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([CH3:16])[C:5]2=1.Cl.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.CCOC(C)=O>N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:15][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=3)[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([CH3:16])[C:5]2=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 593375486-chloro-4-methyl-9H-beta-carbolin-8-ylamine

Produkt 1

HCID 11302139N-(6-chloro-4-methyl-9H-beta-carbolin-8-yl)-nicotinamideAusbeute 8,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 6-chloro-4-methyl-9H-β-carbolin-8-ylamine (43 mg, 0.19 mmol) in pyridine (4 ml) was stirred at RT under an argon atmosphere. Nicotinoyl chloride hydrochloride (40 mg, 0.22 mmol) was added thereto and the reaction mixture was stirred for 12 hr. The solution was diluted with H2O (5 ml) and poured into a separatory funnel containing H2O (5 ml) and EtOAc (25 ml). The reaction mixture was shaken and the layers were separated. The aqueous layer was extracted with EtOAc (2×25 ml). The combined organic layers were washed with a saturated sodium bicarbonate solution (15 ml), followed by brine, then dried over MgSO4, filtered, and concentrated to yield N-(6-chloro-4-methyl-9H-β-carbolin-8-yl)-nicotinamide (5.2 mg) as an orange viscous oil. 1H-NMR (300 MHz, DMSO-d6): δ 11.67 (s, 1); 10.70 (s, 1); 9.27 (s, 1); 8.83 (s, 2); 8.45 (s, 1); 8.20-8.12 (m, 2); 7.83 (s, 1); 7.66 (s, 1); 2.80 (s, 3). NH4OAc standard conditions. DAD Rf=1.92 min. M+H=337.

Aufarbeitung

  1. additionpoured into a separatory funnel
  2. stirringThe reaction mixture was shaken
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc (2×25 ml)
  5. washThe combined organic layers were washed with a saturated sodium bicarbonate solution (15 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-53f6ef4547754956934126c1000345f9
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951801B2

Notizen zur Reaktion

Wird geladen…