Potassium Carbonate → N-cyclopropyl-4-(4-isobutylamino-imidazo[1,2-a]quinoxalin-1-yl)-benzamide

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Reaktionsgleichung

Br[C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]2=[N:4][CH:3]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH:20]1([NH:23][C:24]([C:26]2[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=2)=[O:25])[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:20]1([NH:23][C:24](=[O:25])[C:26]2[CH:31]=[CH:30][C:29]([C:2]3[N:6]4[C:7]5[C:12]([N:13]=[C:14]([NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]4=[N:4][CH:3]=3)=[CH:11][CH:10]=[CH:9][CH:8]=5)=[CH:28][CH:27]=2)[CH2:21][CH2:22]1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

(1-bromo-imidazo[1,2-a]quinoxalin-4-yl)isobutyl-amine (20 mg, 0.07 mmol), [4-[(cyclopropylamino)carbonyl]phenyl]-boronic acid (21.8 mg, 0.11 mmol), Pd(dppf)Cl2 (1.26 mg, 0.007 mmol) and potassium carbonate (212 μL, 1M in water) were combined in 2 mL NMP in a sealed vial and heated at 140° C. under microwave irradiation for 40 min. After cooling, the solution was filtered and subjected to preparative HPLC to give N-cyclopropyl-4-(4-isobutylamino-imidazo[1,2-a]quinoxalin-1-yl)-benzamide (2.86 mg, 10%): 1H-NMR (300 MHz, d6-DMSO): δ=8.60 (1H, d), 7.97 (2H, d), 7.71 (1H, t), 7.69 (2H, d), 7.54 (1H, d), 7.52 (1H, s), 7.28 (1H, dd), 7.19 (1H, d), 6.91 (1H, dd), 3.39 (2H, dd), 2.86 (1H, m), 2.09 (1H, sept), 0.96 (6H, d), 0.70 (2H, d), 0.55 (2H, d) ppm; UPLC-MS: RT=1.14 min; m/z (ES+) 400.4 [MH+]; required MW=399.5.

Aufarbeitung

temperatureAfter cooling
filtrationthe solution was filtered

Quellen und Nachweise

ORD-Eintrag: ord-aae74841c3884ed980c584dca4423b09
Quelldatensatz: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08729082B2

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