4-Methylmorpholine → HCID 24983479, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL, single-neck, round-bottomed flask was charged with 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (42 mg, 0.1694 mmol) and THF (2 mL) under nitrogen and cooled to −78° C. on a dry ice bath. N-methylmorpholine (0.037 mL, 0.34 mmol), and isobutyl chloroformate (0.019 ml, 0.15 mmol) were added. After 15 minutes 4-(2-(3-(diethylamino)prop-1-ynyl)thieno[3,2-b]pyridin -7-yloxy)benzenamine (40 mg, 0.11 mmol) in THF (1 mL) was added, and the reaction was allowed to warm to room temperature overnight. The reaction mixture was concentrated and the residue was purified on a Biotage 15M column (95:5 EtOAc/MeOH). The product was a white waxy solid (0.8 mg, 2%). 1H NMR (CDCl3, 400 MHz) δ 8.47 (d, J=5.5 Hz, 1H), 7.57 (s, 1H), 7.49 (m, 2H), 7.14 (m, 2H), 6.68 (br s, 1H), 6.54 (d, J=5.5 Hz, 1H), 3.98 (d, J=6.6 Hz, 2H), 3.72 (s, 2H), 2.65 (q, J=7, 14 Hz, 4H), 2.00 (m, 1H), 1.14 (t, J=7.0 Hz, 6H), 0.99 (d, J=7.0 Hz, 6H). LRMS (ESI pos) m/e 452 (M+1).

Provenance & Evidence