1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-beta-carbolin-8-yl]-2-methyl-nicotinamide

HRID 12215

Reaktionsgleichung

Reaktionsgleichung von HRID 12215
[NH2:1][C:2]1[CH:3]=[C:4]([Cl:22])[CH:5]=[C:6]2[C:14]=1[NH:13][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[C:7]2=1.[CH3:23][C:24]1[N:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](O)=[O:27].CCN=C=NCCCN(C)C>N1C=CC=CC=1>[Cl:22][C:4]1[CH:5]=[C:6]2[C:14](=[C:2]([NH:1][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][CH:31]=[N:32][C:24]=3[CH3:23])[CH:3]=1)[NH:13][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[C:7]2=1

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6433732-Methylnicotinic acidHCID 86595095N-(8-amino-6-chloro-9H-beta-carbolin-4-yl)-2,2,2-trifluoro-acetamide

Produkt 1

HCID 86595096N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-beta-carbolin-8-yl]-2-methyl-nicotinamideAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

N-(8-amino-6-chloro-9H-β-carbolin-4-yl)-2,2,2-trifluoro-acetamide (90 mg, 0.274 mmol, 1 equiv.) and 2-methylnicotinic acid (45 mg, 0.329 mmol, 1.2 equiv.) were dissolved in 1.5 ml of anhydrous pyridine under N2. EDCI (84 mg, 0.438 mmol, 1.6 equiv.) was added in one portion and the reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with water and the resulting dark solids captured by filtration. These solids were titurated in a 3:1 methanol—DMSO solution to give N-[6-chloro-4-(2,2,2-trifluoro-acetylamino)-9H-β-carbolin-8-yl]-2-methyl-nicotinamide as light yellow solids (41 mg, 3%).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. filtrationthe resulting dark solids captured by filtration

Quellen und Nachweise

ORD-Eintrag
ord-729d7e71038f4e0fbe7010d97014baa8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727985B2

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