1,2-Dichloroethane → 4-(2-(4-Methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetamido)adamantan-1-carboxamide

Participants

Reaction Steps

To 4-aminoadamantan-1-carboxamide hydrochloride (900 mg, 3.9 mmol) in DMSO (40 mL) and i-prOH (50 mL), were added DIPEA (2.5 g, 19.5 mmol), 2-(4-methyl-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetic acid (1.8 g, 4.7 mmol), EDC (894 mg, 4.7 mmol) and HOBT (632 mg, 4.7 mmol), and then agitated for 5 hr at room temperature. After the addition of water, the resultant extracted with EtOAc, dried (Na2SO4), filtered and concentrated under reduced pressure, followed by column chromatography (MeOH/DCM 5%), finally giving the title compound (solid, 980 mg, y=64%) E-form. 1H NMR (300 MHz, DMSO-d6) δ 7.41 (d, J=2.4 Hz, 1H), 7.39 (d, J=2.4 Hz, 1H), 5.58 (s, 1H), 5.35 (s, 1H), 4.35 (d, J=17 Hz, 1H), 4.08-4.00 (m, 2H), 3.91-3.85 (m, 1H), 3.73 (d, J=17 Hz, 1H), 3.30-3.17 (m, 2H), 2.70-2.54 (m, 1H), 2.17-1.54 (m, 13H); LC/MS MH+ 563

Provenance & Evidence