Water → HCID 178437524, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 13a (95 mg, 0.21 mmol), sodium azide (20 mg, 0.31 mmol) and ammonium chloride (16 mg, 0.31 mmol) in DMF (3 mL) was heated at 130° C. overnight. The reaction mixture was cooled to rt and water (20 mL) was added. The mixture was extracted with DCM/MeOH (9:1 v/v, 2×100 mL). The combined organic layers were washed with brine, and dried over Na2SO4. The mixture was filtered and concentrated to obtain a residue, which was washed with MeOH (2×2 mL). The resulting solid was purified by flash column chromatography on silica gel (0-20% MeOH/DCM) to give compound 13b as an orange solid. 1H-NMR (400 MHz, CDCl3+CD3OD) δ (ppm): 8.27 (d, J=8.3 Hz, 2H), 8.09-8.14 (m, 1H), 8.02-8.07 (m, 1H), 8.00 (d, J=5.6 Hz, 1H), 7.84-7.92 (m, 3H), 7.73-7.80 (m, 2H), 7.65-7.72 (m, 2H), 7.46-7.53 (m, 1H), 6.12 (d, J=5.6 Hz, 1H), 4.04-4.11 (m, 4H), 3.96-4.02 (m, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C28H23N9O: 502.2 (M+H). Found 502.5.

Provenance & Evidence