1-(furan-2-yl)ethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 25 mL round bottom flask, fitted with magnetic stirrer, 15 mL of tetrahydrofuran, 2.1 mmol (1.5 eq.) of pyridine and 1.54 mmol (1.1 eq.) of 1-(furan-2-yl)ethanamine were added. 1.4 mmol of 2-isopropyl-2,3-dimethylbutanoyl chloride (prepared by hydrolysis of 2-isopropyl-N,2,3-trimethylbutanamide, WS-23 with NaNO2 in H2SO4 and subsequent acid chloride formation with SOCl2) were added and the mixture was stirred at room to temperature for 16 hours, overnight. The reaction mixture was extracted with MTBE and HCl (1N in water). The organic layer was washed with NaOH (1N in water) and brine, dried over MgSO4 and concentrated. The crude product was purified by column chromatography, obtaining 160 mg of a beige solid, mp 57-60° C. In a 25 mL round bottom flask, fitted with magnetic stirrer The reaction mixture was extracted with MTBE and HCl (1N in water) The organic layer was washed with NaOH (1N in water) and brine dried over MgSO4 concentrated The crude product was purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared in a similar manner to Example 20 from 2-(4-(6-Cyanopyrazin-2-yl)phenyl)-2-methylpropanoic acid (example 20a) and 1-(furan-2-yl)ethanamine. Yield 35%. 1H NMR (400 MHz, dMSO): δ 1.32-1.33 (d, 3H), 1.49-1.52 (d, 6H), 5.09 (m, 1H), 6.06 (d, 1H), 6.33-6.35 (dd, 1H), 7.49-7.51 (d, 2H), 7.54 (d, 1H), 8.12-8.14 (d, 2H), 9.16 (s, 1H), 9.56 (s, 1H); MS+H (361).