1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(6-chloro-7-methoxy-9H-beta-carbolin-8-yl)-2-methylnicotinamide

HRID 552176

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:17])[C:14]=1[O:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.CCN=C=NCCCN(C)C.[CH3:29][C:30]1[N:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](O)=[O:33]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH:17][C:32](=[O:33])[C:31]3[CH:35]=[CH:36][CH:37]=[N:38][C:30]=3[CH3:29])[C:14]=1[O:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

6-chloro-7-methoxy-9H-β-carbolin-8-ylamine (100 mg, 0.4 mmol), EDCI (125 mg, 0.64 mmol) and 2-methyl nicotinic acid (66 mg, 0.48 mmol) were taken in a round-bottom flask and suspended in pyridine (2 ml). The resulting mixture was heated at 80° C. overnight. The pyridine was then removed by rotary evaporation and 5% Na2CO3 solution was added. The resulting solid that precipitated out was collected by filtration. Chromatographic purification gave the desired product in 50-70% yield. 1H-NMR (300 MHz, DMSO-d6): δ 2.71 (s, 3H), 3.89 (s, 3H), 7.45 (dd, 1H), 8.15 (d, 1H), 8.21 (d, 1H), 8.38 (d, 1H), 8.45 (s, 1H), 8.61 (d, 1H), 8.92 (s, 1H), 10.33 (s, 1H), 11.57 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.77 min. MS (M+H+): 367.1.

Aufarbeitung

customThe pyridine was then removed by rotary evaporation and 5% Na2CO3 solution
additionwas added
customThe resulting solid that precipitated out
filtrationwas collected by filtration
customChromatographic purification

Quellen und Nachweise

ORD-Eintrag: ord-7287754938b64a47b829d8bb1ae7424c
Quelldatensatz: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07951801B2

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