Triphenylphosphine → 2-Oxo-N-(1,2,4-thiadiazol-5-yl)-3-((2-(2,2,2-trifluoroethyl)-1,2,3,4 tetrahydroisoquinolin-8-yl)methyl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

Participants

Reaction Steps

A solution of 1-5 (16.5 mg, 0.037 mmol) and 7-5 (9.02 mg, 0.037 mmol) in THF (368 μl) at RT was treated with PS-bound triphenylphosphine (1.84 mmol/g, 40.2 mg, 0.074 mmol), and DTBAD (16.94 mg, 0.074 mmol). After 30 min, LCMS showed complete consumption of SM. Filtered through Celite and concentrated in vacuo. Dissolved in 245 uL DCM, 123 uL TFA and stirred at RT. After 30 min, diluted with 1 mL MeOH, filtered through Celite and washed with 1 mL MeOH. Concentrated in vacuo and purified by reverse-phase HPLC (C18 column, 5-70% 0.1% TFA/CH3CN:0.1% TFA/H2O) to give 7-6 as an off-white solid. 1H NMR δ (ppm) (DMSO-d6): 8.48 (1H, s), 7.78 (1H, d, J=1.69 Hz), 7.67 (1H, dd, J=8.28, 1.72 Hz), 7.25 (1H, d, J=8.33 Hz), 7.14-7.09 (2H, m), 6.92 (1H, d, J=6.83 Hz), 5.00 (2H, s), 3.99 (3H, s), 3.54 (3H, d, J=12.20 Hz), 2.90 (2H, s). HRMS C21H19F3N5O4S2 [M+H] calc 526.0825, obs. 526.0806.

Provenance & Evidence