HCID 86689282, compound → HCID 71621463, compound

Participants

Reaction Steps

A 250 mL flask fitted with a stir-bar, condenser, and an Ar inlet was charged with amine 50a (12.5 g, 32.3 mmol) and AcOH (120 mL). The resultant solution was heated in a 100° C. bath for 3 hr. The mixture was cooled and concentrated in vacuo to a pale, orange solid. The solid was partitioned with EtOAc (150 mL) and saturated NaHCO3 (100 mL). The organic phase was washed with brine (100 mL), filtered through phase separation paper, and concentrated in vacuo to an orange oil. The oil was crystallized with hexanes (25 mL), filtered, and rinsed with hexanes (2×15 mL). The material dried to give 9.9 g of Compound #1 as an off-white solid (83%). 1H NMR (300 MHz, CDCl3): δ 7.66 (d, 1H), 7.21 (t, 1H), 6.94 (dd, 1H), 6.82 (d, 1H), 6.71-6.62 (m, 2H), 6.56 (dd, 1H), 5.33 (s, 2H), 4.10 (qt, 2H), 4.05 (t, 2H), 4.03 (qt, 2H), 2.35 (nonet, 1H), 1.48 (t, 3H), 1.43 (t, 3H), 0.98 (d, 6H) ppm. HPLC analysis (0:10:90 H2O:A1:MeOH) showed a purity of 99% with a retention time of 4.6 min.

Provenance & Evidence