Triethylamine → HCID 25108833, compound

Participants

Reaction Steps

HATU (67 mg, 0.18 mmol) and triethylamine (50 μL, 0.35 mmol) were added to a solution of sodium 1-(2-fluoro-4-iodo-benzyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (49 mg, 0.12 mmol) and O-cyclopropylmethyl-hydroxylamine hydrochloride (21.8 mg, 0.178 mmol) in DMF (500 μL). The reaction mixture was stirred at room temperature for 18 h, then a further 11 mg (0.09 mmol) of O-cyclopropylmethyl-hydroxylamine hydrochloride, 33 mg (0.09 mmol) of HATU, and 50 μL (0.35 mmol) of triethylamine was added. Stirring was continued for a further 18 h, then the reaction mixture was poured into ethyl acetate (15 mL). The organic layer was washed with a 1:1 solution of saturated NaHCO3 and brine (10 mL), dried over Na2SO4, filtered and concentrated to afford a yellow oil. The crude product was purified by reversed phase HPLC to afford the title compound as a white powder (TFA salt, 39 mg, 57%). LCMS (Method C): RT=3.17 min, M+H+=466. 1H NMR (DMSO-D6): δ=0.21 (m, 2H), 0.51 (m, 2H), 1.00 (m, 1H), 3.60 (d, J=7.2 Hz, 2H), 5.96 (s, 2H), 6.61 (t, J=8.0 Hz, 1H), 7.33 (s, 1H), 7.47 (dd, J=8.0, 1.2 Hz, 1H), 7.68 (dd, J=9.6, 1.6 Hz, 1H), 8.24 (d, J=6.4 Hz, 1H), 8.43 (d, J=6.4 Hz, 1H), 9.52 (s, 1H).

Provenance & Evidence