Ethoxyacetyl chloride → 1-(2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol
Reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=O)[CH3:2].[OH:8][C:9]([CH3:24])([CH3:23])[CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][N:20]=2)[N:15]=[CH:14][C:13]=1[NH2:22]>N1C=CC=CC=1>[CH2:1]([O:3][CH2:4][C:5]1[N:11]([CH2:10][C:9]([CH3:24])([OH:8])[CH3:23])[C:12]2[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1)[CH3:2]Participants
4
Procedure
Under a nitrogen atmosphere, ethoxyacetyl chloride (19.1 g, 0.156 mol) was added over a period of 12 minutes to a mixture of N4-(2-hydroxy-2-methylpropyl)[1,5]naphthyridin-3,4-diamine (28.95 g, 0.125 mol) and pyridine (300 mL). The reaction mixture was stirred at ambient temperature for 4 hours and then heated at reflux for 4 hours. The reaction mixture was allowed to cool to ambient temperature overnight and then concentrated under reduced pressure. The residue was dissolved in 5% aqueous potassium carbonate (200 mL) and then extracted with dichloromethane (200 mL). The extract was filtered to remove some insoluble material, dried over magnesium sulfate, filtered, and then concentrated under high vacuum. The residue was dissolved in dichloromethane (150 mL) and put through a short column of neutral alumina. The eluant was concentrated to provide 31.9 g of 1-(2-ethoxymethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol.