Sodium Iodide → 4-Methoxyquinoline-2-carboxamide

HRID 890402

Reaktionsgleichung

C(OC(N1CCN(C(C([NH:21][C:22]([C:24]2[CH:33]=[C:32]([O:34][CH3:35])[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)=[O:23])CC2N=CNC=2)=O)CC1)=O)C.C(=O)([O-])[O-].[K+].[K+].[Na+].[I-]>CN(C=O)C>[NH2:21][C:22]([C:24]1[CH:33]=[C:32]([O:34][CH3:35])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=1)=[O:23]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-2-(imidazol-4-yl)ethyl]aminocarbonyl-4-methoxyquinoline (69 mg, 0.14 mmol) in DMF (2 mL) was added t-butyl bromo acetate (0.026 mL, 1.2 eq.), potassium carbonate (30 mg, 1.5 eq), NaI (2.0 mg, 0.1 eq.). The reaction mixture was heated at 50° C. for 1 hour. Evaporation followed by flash column chromatography with 2%–3% MeOH in methylene chloride afforded 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-2-(1-(t-butoxycarbonyl)methyl)imidazol-4-yl)ethyl]-aminocarbonyl-4-methoxyquinoline (25 mg) which was treated with neat trifluoroacetic acid (0.5 mL) for 1.5 hours at ambient temperature. Repeated evaporation of the solvents and treatment with methylene chloride afforded 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-2-(1-(carboxymethyl)imidazol-4-yl)ethyl]-aminocarbonyl-4-methoxyquinoline (27 mg) as a trifluoroacetic acide salt: NMR (DMSO) 1.20 (t, 3), 3.2–3.6 (m, 11), 4.05 (q, 2), 4.1 (s, 3), 5.0 (s, 2), 5.3 (m, 1), 7.45 (s, 1), 7.5 (s, 1), 7.65 (t, 1), 7.8 (t, 1), 8.05 (d, 1), 8.16 (d, 1), 8.95 (s, 1) ppm.

Aufarbeitung

customEvaporation

Quellen und Nachweise

ORD-Eintrag: ord-3e098c6c48fc44caa97e1ac101eb47dc
Quelldatensatz: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06995156B2

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