2-Methylbut-3-yn-1-ol → 2-(3-Hydroxy-3-methylbut-1-yn-1-yl)-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-9-carboxamide

Participants

Reaction Conditions

Reaction Steps

Into a 20-mL sealed tube was placed a solution of methyl 2-(3-hydroxy-3-methylbut-1-yn-1-yl)-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-9-carboxylate (100 mg, 0.31 mmol, 1.00 equiv, prepared by reaction of methyl 2-chloro-6,7-dihydroimidazo[1,2-d]pyrido[3,2-b][1,4]oxazepine-9-carboxylate with 2-methylbut-3-yn-ol similar to as described in General Procedure G. The crude mixture was reacted with NH3.H2O (2 mL, 37%) in 1,4-dioxane (4 mL) similar to as described in General Procedure M. The resulting solution was stirred overnight at 100° C., diluted with 10 mL of H2O, extracted with 3×50 mL of ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum. The crude product was purified by Flash-Prep-HPLC with the following conditions (CombiFlash-1): Column, silica gel; mobile phase, DCM/MeOH (100:1-10:1); Detector, UV 254 um. This resulted in 423 mg (44%) of the titled compound as a light yellow solid.

Provenance & Evidence