Iodoethane → HCID 66829252, compound

Participants

Reaction Steps

A solution of 2-hydroxy-N-[(2S)-2-hydroxy-3-(4-{5-[5-(isopropylamino-methyl)-4-methyl-thiophen-2-yl]-[1,2,4]oxadiazol-3-yl}-2,6-dimethyl-phenoxy)-propyl]-acetamide (284 mg, 0.448 mmol, Example 91), ethyl iodide (423 mg, 2.69 mmol) and DIPEA (354 mg, 2.69 mmol) in DMF (3 mL) is stirred at rt for 1 h, then at 40° C. for 17 h before another portion of DIPEA (54 mg, 0.421 mmol) and ethyl iodide (304 mg, 1.95 mmol) is added. Stirring is continued at 40° C. for 20 h. The mixture is diluted with aq. sat. NH3 (1 mL) and separated by prep. HPLC (Waters XBridge Prep C18, 75×30 mm ID, 10 μm, gradient of acetonitrile in water containing 0.5% of sat. aq. NH3) to give the title compound (94 mg) as a colourless resin; LC-MS*: tR=1.08 min; [M+1]+=517.32.

Provenance & Evidence