Lithium hydroxide, monohydrate → HCID 178490977, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-Methoxyphenyl)-2-thiourea (0.01 g, 0.054 mmol) was added to a solution of the product from Example 48A (0.02 g, 0.054 mmol) in ethanol (0.5 mL) and heated at 80° C. for 1 h. The solvent was then removed in vacuo and the residue taken up in tetrahydrofuran (1 mL) and water (0.5 mL). Lithium hydroxide monohydrate (0.005 g, 0.1 mmol) was added to the reaction mixture and stirred at 50° C. for 3 h. The solvents were then removed and the residue purified by RP-HPLC to afford the title compound as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.09-1.18 (m, 2 H), 1.45-1.54 (m, 2 H), 1.62-1.69 (m, 1 H), 1.70-1.77 (m, 1 H), 1.80-1.88 (m, 4 H), 2.13 (d, J=7 Hz, 2 H), 3.78 (s, 3 H), 6.54 (dd, J=8.24, 1.83 Hz, 1 H), 7.10-7.16 (m, 1 H), 7.20-7.27 (m, 1 H), 7.29 (d, J=8.24 Hz, 2 H), 7.51-7.56 (m, 1 H), 7.79-7.83 (d, J=8.24 Hz, 2 H), 10.25 (s, 1 H), 1.2.05 (s, 1 H): MS (ESI) m/e 423.2 (M+H).

Provenance & Evidence