Triphenylphosphine → 3-((3-Chloroisoquinolin-8-yl)methyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (11-3) and (3-chloroisoquinolin-8-yl)methanol in THF (697 μl) at 0° C. was treated with ps-triphenylphosphine (73.1 mg, 0.279 mmol) (152 mg resin-bound PPh3, 1.84 mmol PPh3/g of resin), then (E)-di-tert-butyl diazene-1,2-dicarboxylate (64.2 mg, 0.279 mmol). Reaction mixtured was monitored at 0° C. After stirring at 0° C. for 2 h, the reaction was filtered and concentrated in vacuo. Residue was dissolved in 1 mL of DCM and treated with 0.25 mL of TFA. After stirring at RT for 30 minutes, the solvent and TFA were removed in vacuo. Purified by reverse phase chromatography (10-95% MeCN in water w/0.1% TFA, C18 column) to yield 25-2. 1H NMR δ (ppm)(CH3OH-d4): 9.48 (1H, s), 8.20 (1H, s), 7.96 (1H, s), 7.90 (1H, d, J=8.36 Hz), 7.81 (1H, d, J=5.48 Hz), 7.75 (1H, t, J=7.75 Hz), 7.57 (1H, d, J=7.08 Hz), 7.12 (1H, d, J=9.32 Hz), 5.69 (2H, s). HRMS [M+H]C19H11ClFN5O4S2 calc'd 491.9998. Found 492.0001.

Provenance & Evidence