Dimethyl Sulfoxide → HCID 71227381, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-((5S,7S)-7-((6-cyano-1H-benzo[d]imidazol-1-yl)methyl)-7-methyl-2-oxo-1-oxa-3-azaspiro[4.5]decan-3-yl)-4-methylpyridin-2-yl trifluoromethanesulfonate (100 mg, 0.177 mmol) and morpholine (0.077 mL, 0.887 mmol) in Dimethyl Sulfoxide (DMSO) (1.5 mL) was heated in the microwave for 35 minutes at 100° C. The solution was purified by reverse phase HPLC (Waters Sunfire 30×150 mm Acetonitrile: Water 0.1% TFA 10-50%, 50 mL/min, 15 min) to afford the bis-TFA salt of 1-(((5S,7S)-7-methyl-3-(4-methyl-6-morpholinopyridin-3-yl)-2-oxo-1-oxa-3-azaspiro[4.5]decan-7-yl)methyl)-1H-benzo[d]imidazole-6-carbonitrile (60 mg, 46%). 1H NMR (400 MHz, DMSO-d6) δ 8.65 (s, 1H), 8.46 (s, 1H), 8.08 (s, 1H), 7.88 (d, J=8.28 Hz, 1H), 7.65 (dd, J=8.28, 1.25 Hz, 1H), 6.94 (s, 1H), 4.15-4.25 (m, 2H), 3.67-3.74 (m, 4H), 3.59 (s, 2H), 3.45-3.52 (m, 4H), 2.17 (s, 3H), 2.04 (d, J=13.55 Hz, 1H), 1.92 (d, J=14.56 Hz, 1H), 1.58-1.77 (m, 3H), 1.30-1.52 (m, 3H), 1.08 (s, 3H). MS (m/z) 501.3 (M+H+).

Provenance & Evidence