Isopropyl Acetate → N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(2,2-dimethoxyethyl)cyclohexanamine (21.5 g) in tetrahydrofuran (30 mL) was added to a solution of 3-(3-(1-methyl-1H-pyrazol-4-yl)phenethoxy)propanoic acid in tetrahydrofuran (105 mL) at 20° C. Tetrahydrofuran (15 mL) was added, followed by triethylamine (51.8 mL), followed by a solution of T3P in tetrahydrofuran (121.9 mL of a 1.62M solution). The solution was stirred at 20° C. for 1 h then cooled to 10° C. Pre-chilled (10° C.) 0.5M sodium bicarbonate solution (225 mL) was added, followed by iso-propyl acetate (150 mL). After mixing the layers were separated and the organic layer washed with 20% w/w sodium chloride solution (150 mL), then evaporated to dryness to afford the subtitled compound as a brown oil (48.6 g). MS [M+H-MeOH]+=412.20 (100%) (MultiMode+) [M+H]+=444.20 (MultiMode+) 1H NMR (300 MHz, CDCl3) δ 7.75 (s, 1H), 7.62 (s, 1H), 7.33-7.23 (m, 3H), 7.10-7.03 (m, 1H), 4.61 (t, 0.7H), 4.36 (t, 0.3H), 3.94 (s, 3H), 3.79 (q, 2H), 3.69 (q, 2H), 3.62-3.43 (m, 1.5H), 3.40 (s, 3H), 3.38 (s, 3H), 3.30 (d, 1.5H), 2.89 (q, 2H), 2.69 (quintet, 2H), 1.86-0.99 (m, 10H); approx:2:1 ratio of rotamers

Provenance & Evidence