Reaktionsgleichung
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[CH:2]1.[H-].[Na+].Br[CH2:13][C:14]1[CH:32]=[CH:31][C:17]([C:18]([N:20]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:19])=[CH:16][C:15]=1[O:33][CH3:34]>CN(C)C=O>[CH:26]1([N:20]([CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[C:18](=[O:19])[C:17]2[CH:31]=[CH:32][C:14]([CH2:13][N:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[N:1]=[CH:2][N:3]=[C:4]34)=[C:15]([O:33][CH3:34])[CH:16]=2)[CH2:27][CH2:28][CH2:29][CH2:30]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution of imidazo[4,5-b]pyridine (350 mg, 2.94 mmol) in N,N-dimethylformamide (25 mL), sodium hydride (118 mg, 60% dispersion in mineral oil, 2.94 mmol) was added. After stirring for 2 hr, 4-bromomethyl-3-methoxy-N,N-dicyclopentyl benzamide (1.4 g, 3.57 mmol) was added in small installments over 10 min. The reaction mixture was stirred under argon at 25° C. After 18h, the reaction was quenched by adding acetic acid (0.5 mL) and the solvent was removed under reduced pressure at <45° C. The crude mixture (2 g) was chromatographed (silica gel, CH2Cl2 -MeOH-NH4OH 90-10-1) to give the title compound. (145 mg, 12%) mp 223°-224° C.; Anal calcd. for C25H30N4O2.1.0H2O: C, 68.78; H, 7.39; N, 12.83. Found C, 68.88; H, 7.13; N, 12.55.
Aufarbeitung
- stirringThe reaction mixture was stirred under argon at 25° C
- customAfter 18h, the reaction was quenched
- additionby adding acetic acid (0.5 mL)
- customthe solvent was removed under reduced pressure at <45° C
- customThe crude mixture (2 g) was chromatographed (silica gel, CH2Cl2 -MeOH-NH4OH 90-10-1)
Quellen und Nachweise
- ORD-Eintrag
- ord-5f6478cb34ec4aab8b54f1070336cc48
- Quelldatensatz
- uspto-grants-1993_11
- Patentnummer
- US05262426
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