Trimethylsilyl iodide → HCID 15950040, compound

Participants

Reaction Steps

Trimethylsilyl iodide (0.95 mL, 6.7 mmol) was added to a solution of 3-{[(1S)-1-methyl-2-(methyloxy)ethyl]oxy}-5-[(4-methyl-5-oxo-2,3,4,5-tetrahydro-1,4-benzoxazepin-8-yl)oxy]-N-(3-methyl-1,2,4-thiadiazol-5-yl)benzamide (335 mg, 0.67 mmol) in acetonitrile (20 mL) under an atmosphere of argon and the mixture stirred at RT for 18 hours. The mixture was poured onto saturated sodium hydrogen carbonate solution (50 mL), the acetonitrile removed in vacuo, and the aqueous layer extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with sodium thiosulphate solution, brine, dried (MgSO4) and evaporated in vacuo to a residue which was chromatographed on silica, eluting with ethyl acetate then with 2% methanol in DCM, to give the desired compound as a colourless solid (50 mg). 1H NMR δ (CDCl3): 1.3 (d, 3H), 2.5 (s, 3H), 3.2 (s, 3H), 3.6 (t, 2H), 3.75 (m, 2H), 4.4 (t, 2H), 4.55 (m, 1H), 6.55 (d, 1H), 6.7 (dd, 1H), 6.8 (d, 1H), 7.2 (s, 1H), 7.25 (s, 1H), 7.85 (d, 1H); m/z 485 (M+H)+

Provenance & Evidence