Triphenylphosphine → 3-((3-Aminoisoquinolin-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

N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (11-3, 50 mg, 0.107 mmol), (E)-di-tert-butyl diazene-1,2-dicarboxylate (49.4 mg, 0.214 mmol) and triphenylphosphine (56.2 mg, 0.214 mmol) were added to a 5 mL RB flask. Then THF was added and r×n mixture was stirred at 0° C. for 10 min before addition of tert-butyl (8-(hydroxymethyl)isoquinolin-3-yl)carbamate (29.4 mg, 0.107 mmol) in THF. 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 27-5. 1H NMR δ (ppm)(DMSO-d6): 9.08 (1H, s), 7.65 (1H, d, J=5.39 Hz), 7.47 (1H, d, J=8.47 Hz), 7.34-7.26 (2H, m), 6.92 (1H, d, J=7.03 Hz), 6.65 (1H, s), 5.50 (2H, s). HRMS [M+H]C19H13FN6O4S2 calc'd 473.0496. Found 473.0499.

Provenance & Evidence