Dimethylformamide → HCID 59004612, compound

Participants

Reaction Conditions

Reaction Steps

compound 8 (75 mg, 0.223 mmol), 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (45.2 mg, 0.245 mmol), potassium carbonate (92.4 mg, 0.669 mmol) and anhydrous dimethylformamide (5 mL) were charged to a small, argon purged flask fitted with a magnetic stirbar and resulting solution heated in an oil bath at 65° C. for 20 hours. After cooling to room temperature the mixture was diluted with H2O and ethyl acetate, transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine (twice), dried over magnesium sulphate, filtered and concentrated to afford crude solid. The crude product was purified using dry silica gel column chromatography eluting with 25 mL portions of solvent system (2M NH3 in MeOH:CH2Cl2, 2.5:97.5) to yield a yellow residue, 12 (100 mg, quantitative). 1H NMR (DMSO-d6) δ 1.35-1.45 (m, 2H), 1.58-1.64 (m, 3H), 1.72-1.88 (m, 1H), 1.97-2.05 (m, 2H), 2.08 (s, 3H), 2.86-2.95 (m, 1H), 4.15 (t, 2H, J=7.7 Hz), 4.29 (s, 2H), 6.49 (s, 1H), 7.33-7.43 (m, 4H), 7.57 (d, 1H, J=9.1 Hz), 8.00 (dd, 1H, J=9.1, 2.2 Hz), 8.50 (d, 1H, J=2.2 Hz); ESI-MS (m/z, %): 448 (MH+, 100%).

Provenance & Evidence