Diisopropylcarbodiimide → HCID 57722719, compound

Participants

Reaction Steps

To a solution of the lithium salt of [6-cyano-3-(2,2-difluoro-2-pyridin-2-yl-ethylamino)-2-fluoro-phenyl]-acetic acid (75 mg, 0.22 mmol), prepared essentially as described in Example 1k, in N,N-dimethylformamide (0.250 mL) and methylene chloride (0.750 mL) was added pentafluorophenol (121 mg, 0.66 mmol), pyridine hydrochloride (52 mg, 0.45 mmol), dimethylaminopyridine (14 mg, 0.11 mmol), and finally diisopropylcarbodiimide (0.038 mL, 0.24 mmol). The mixture was stirred at room temperature for 24 h. The solvents were evaporated under high vacuum and the residue was purified by flash column chromatography (20-30% ethyl acetate in hexanes) to yield the desired compound (51 mg, 50%). 1H-NMR (300 MHz, CDCl3) δ 8.68 (d, J=5.5 Hz, 1H), 7.84 (td, J=7.8 Hz, 1.7 Hz, 1H), 7.69 (dt, J=7.9 Hz, 1.1 Hz, 1H), 7.40-7.45 (m, 1H), 7.35 (dd, J=8.6 Hz, 1.3 Hz, 1H), 6.86 (t, J=8.5 Hz, 1H), 5.05 (br s, 1H), 4.12-4.23 (m, 4H). LC/MS (m/z) [M+1]+ 502.3 (calculated for C22H12F8N3O2, 502.3).

Provenance & Evidence