HCID 118235731, compound → HCID 118235817, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of the sodium salt of Example 46 (207 mg, 0.38 mmol) and tetra-n-butylammonium chloride (42 mg, 1.5 mmol) in DMSO (2.5 mL) was heated under microwave irradiation, in a sealed tube, to 180° C. for 10 minutes. The reaction mixture was diluted with EtOAc (30 mL), and washed with HCl (1M, 20 mL), water (2×20 mL) and brine (20 mL), then the organic layers were dried over MgSO4 and the solvent was removed. The resulting crude yellow gum (270 mg) was purified by uv-directed preparative HPLC (pH 10 method eluting with 50-65% solvent B) to give the title compound (90 mg, 41%) as a colourless gum. δH (400 MHz, CD3OD) 8.39 (s 2H), 8.10 (d, 1H, J 7.3 Hz), 7.32-7.26 (m 2H), 7.21 (m, 1H), 7.16 (t, 1H, J 7.7 Hz), 7.10-7.08 (m, 1H), 6.92 (t, 1H, J 74 Hz), 4.42 (t, 2H, J 4.0 Hz), 4.38 (s, 2H), 4.18 (t, 2H, J 6.4 Hz), 3.40-3.37 (m, 2H), 2.42 (s, 3H), 2.17 (d, 2H, J 13.6 Hz), 1.69 (m, 2H), 1.51-1.42 (m, 4H), 1.26 (s, 3H), 0.99 (t, 3H, J 7.3 Hz). HPLC-MS (pH 10): MH+ m/z 582.8, RT 3.04 minutes.

Provenance & Evidence