Phenylacetyl isothiocyanate → 1-(4-(2-(Methylsulfonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thiourea

Participants

Reaction Steps

To a suspension of 237 (20 mg, 0.059 mmol) in THF (10 mL) was added 2-phenylacetyl isothiocyanate (26 mg, 0.146 mmol). The reaction mixture was stirred for 2 hours, concentrated under reduced pressure and the residue was purified by column chromatography, eluent EtOAc/MeOH (19:1), to afford a solid material that was dissolved in a minimum MeOH and precipitated with hexane to afford title compound 238 (9.6 mg, 31%) as a white solid. 1HNMR: (DMSO-d6) δ (ppm): 12.48 (s, 1H), 11.81 (s, 1H), 8.69(d, J=5.5 Hz, 1H), 8.36 (s, 1H), 8.03(d, J=12.13 Hz, 1H), 7.55 (s, 2H), 7.36-7.30 (m, 2H), 7.30-7.24 (m, 3H), 6.86(d, J=5.5 Hz, 1H), 3.83 (s, 2H), 3.54 (s, 3H). MS (m/z): 516.2.

Provenance & Evidence