Diisopropylcarbodiimide → (S)-tert-butyl 1-((4-(5-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methylamino)-1-oxopropan-2-ylcarbamate

Participants

Reaction Steps

A solution of compound 16 (73 mg, 0.120 mmol) in DMF (1.0 mL) and DIC (0.1 mL, 0.642 mmol) was heated to 100 degrees for 13 hours. The reaction was concentrated down to a brown gum and then applied onto a 12M Biotage column and eluted with 0-5% methanol and dichloromethane to give 72 mg of a semi-purified compound. This material was further purified by preparative HPLC (C18 Aquasil 20×250 mm; 40-85% methanol in water in 45 minutes at 10 mL/min) to give compound 17 (20.3 mg, 29%) as a white crust. LRMS (ESI): calc. 592.2; found 493.2 (MH-Boc)+, 593.3 (MH)+.

Provenance & Evidence