Hydrochloric Acid → HCID 11202787, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of compound 32 (100 mg, 0.22 mmol) in THF (4 mL) was added NaI (100 mg, 0.67 mmol) and the mixture stirred for 1 h. The reaction was cooled to 5° C. and a solution of morpholine (0.029 mL, 0.33 mmol) in THF (2 mL) was added over 1 h. After stirring for 1 h, the reaction was diluted with EtOAc (40 mL) and poured into a mixture of ice water (30 mL) and 0.1 N HCl (10 mL). The layers were separated and the organic layer was washed with brine (40 mL), dried (MgSO4) and concentrated. Et2O (8 mL) was added and the mixture was stirred for 2 h. The resulting solid was filtered, rinsed with Et2O and dried to afford the title compound, 31, as a yellow solid (68 mg, 61%). 1HNMR (400 MHz, DMSO-d6): δ 0.85 (t, 3H), 2.39 (q, 2H), 2.52 (br, 4H), 3.43 (br, 2H), 3.55 (br, 4H), 6.50 (d, J=15.9 Hz, 1H), 6.80 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 7.09-7.19 (m, 5H), 7.24 (d, J=8.1 Hz, 2H), 7.58 (d, J=15.9 Hz, 1H), 769 (d, J=8.1 Hz, 2H), 12.33 (br s, 1H); MS m/z 498 (M+H)+.

Provenance & Evidence