Pyridine → HCID 22278713, compound

Participants

Reaction Steps

A 25 mL dry round bottom flask equipped with a magnetic stir bar was charged with a solution of 3-{[3,6-diethyl-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-yl]amino}butan-1-ol (Example 39, 192 mg, 0.5 mmol) in CH2Cl2 (5 mL). The reaction was cooled with an ice bath and then treated with pyridine (0.044 mL, 0.55 mmol) followed by acetyl chloride (0.039 mL, 0.55 mmol). The solution turned from clear to a light yellow. The ice bath was removed and the reaction was stirred at ambient temperature for 2 hours. The reaction was diluted with CH2Cl2, washed twice with water, once with brine, dried with MgSO4, filtered and concentrated to give 217 mg of a crude oil. This material was purified by Biotage MPLC (40 g column, 20% ethyl acetate in heptane) to give 208 mg (97%) of 3-{[3,6-diethyl-5-(3-methoxy-5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-yl]amino}butyl acetate as a clear oil. Rf 0.15 (5% acetone in toluene). OAMS supporting ions at: ESI+ 426.1.

Provenance & Evidence