1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (R)-1-(3-(Ethoxycarbonyl)-1,2,4-oxadiazol-5-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethyl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

Participants

Reaction Steps

A stirred solution of (R)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-2-(4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carbonyloxy)propanoic acid (28.5 mg, 0.0471 mmol) in anhydrous diglyme (2.5 mL) was treated with ethyl 2-amino-2-(hydroxyimino)acetate (6.54 mg, 0.0495 mmol) and 1-[3-(dimethylamino)propyl]3-ethylcarbodiimide hydrochloride (0.49 mg, 0.0495 mmol) at room temperature. The mixture was stirred overnight at room temperature and then overnight at 110° C. After cooling to room temperature and removal of the solvent in vacuo, the crude compound was purified using preparative HPLC to afford a tan gum (11.2 mg, 34%). 1H-NMR (CDCl3, 400 MHz) δ 8.0 (s,1H), 7.58 (s, 1H), 7.57 (s, 1H), 7.46 (m, 1H), 7.30 (s,1H), 7.24-7.20 (m, 2H), 6.93 (s,1H), 6.17-6.15 (m, 1H), 5.71 (s, 2H), 4.50-4.48 (m, 2H), 4.29-4.20 (m, 2H), 3.65-3.55 (m, 2H), 3.40-3.38 (m, 2H), 3.20-2.81 (m, 4H), 2.59 (s, 3 h), 2.03-1.72 (m, 4H), 1.44-1.38 (m, 3H), 0.95-0.86 (m, 2H), −0.045 (s, 9H).

Provenance & Evidence