2,2-Dimethyl-1,3-propanediamine → HCID 57896774, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carbonitrile (30 mg, 0.081 mmol) in EtOH (2 mL) was added 2,2-dimethylpropane-1,3-diamine (41.5 mg, 0.406 mmol) and sulfur (41.7 mg, 0.162 mmol). The reaction was heated to 80° C. and stirred at that temperature for 6 h. LCMS analysis identified the product as the predominant component of the reaction mixture. The reaction mixture was concentrated in vacuo and the resulting paste was purified by flash column chromatography using a gradient elution of hexanes with 20-100% EtOAc to provide 7-(5,5-dimethyl-1,4,5,6-tetrahydropyrimidin-2-yl)-1-(4-(trifluoromethyl)phenylsulfonyl)-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine (18.7 mg, 0.039 mmol, 48.1% yield) as an off white solid. LCMS (+ESI) m/z=455.1 [M+H]+; 1H-NMR (CD3OD) δ 8.51 (d, 1H), 8.26 (d, 1H), 8.01 (d, 2H), 7.90 (d, 2H), 3.98 (s, 4H), 3.15 (s, 4H), 1.05 (s, 6H).

Provenance & Evidence