2-Methylpropylenediamine → HCID 178428470, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonitrile (30 mg, 0.081 mmol) in toluene (2 mL) was added 1,2-diamino-2-methylpropane (200 μL, 1.908 mmol) and sulfur (20.84 mg, 0.081 mmol). The reaction was heated to 95° C. and stirred at that temperature for 2 h. The reaction mixture was load directly onto a silica gel column and was purified by flash column chromatography using a gradient elution of hexanes with 20-100% EtOAc to provide 7-(4,4-dimethyl-4,5-dihydro-1H-imidazol-2-yl)-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (12 mg, 0.026 mmol, 31.9% yield) as an off white solid. LCMS (+ESI) m/z=441.1 [M+H]+; 1H-NMR (CDCl3) δ 8.54 (d, 1H), 8.50 (d, 1H), 7.81 (d, 2H), 7.76 (d, 2H), 3.94 (dd, 2H), 3.87 (dd, 2H), 3.57 (br s, 2H), 1.37 (s, 6H).

Provenance & Evidence