Hydrochloric Acid → HCID 58299574, compound

Participants

Reaction Steps

Compound 269 (120 mg, 220 μmol) was dissolved in dichloromethane (4 mL). Trifluoroacetic acid (0.400 mL, 2203 μmol) was added and the reaction stirred at room temperature for 70 minutes. The reaction was added to aqueous K2CO3 (10%, 30 mL) and extracted thrice with dichloromethane. The combined organics were dried (MgSO4) and evaporated to give a pale yellow solid, 82 mg. This residue was dissolved in dioxane (2 mL) and methanol (2 mL) and 1 mL of a saturated solution of HCl in dioxane was added. ethyl acetate (30 mL) followed by diethyl ether (30 mL) were added to precipitate the HCl salt, which was collected and dried in vacuo to give compound 266 as a yellow solid (77 mg, 84%). 1H NMR (500 MHz, DMSO-d6) δ ppm 9.24-9.36 (m, 4 H) 9.19 (s, 1 H) 8.52 (s, 1 H) 7.97 (s, 1 H) 7.92-7.96 (m, 1 H) 7.44-7.54 (m, 1 H) 6.83 (d, J=8.56 Hz, 1 H) 5.31-5.43 (m, 1 H) 3.94 (s, 3 H) 3.33-3.41 (m, 4 H) 3.21 (br. s., 4 H) 1.95-2.11 (m, 4 H) 1.70 (none, 2 H) ppm.

Provenance & Evidence