Isopropanol → HCID 70688125, compound

Participants

Reaction Steps

To adamantyl amine hydrochloride (127 mg, 0.55 mmol) in DMSO (700 mg), were successively added DIPEA (357 mg, 2.75 mmol), i-PrOH (10 mL), 2-(4-methylene-1,1-dioxido-6-(2,4,6-trichlorophenyl)-1,2,6-thiadiazinan-2-yl)acetic acid (253 mg, 0.66 mmol), EDCI (211 mg, 1.10 mmol) and HOBt (169 mg, 1.10 mmol), and agitated for 12 hr at room temperature. After concentration at 50° C. under reduced pressure, the resultant was added with saturated NH4Cl solution (20 mL), kept to stand for 1 hr for crystallization, filtered and washed three times with water (20 mL). The filtered solid was purified by column chromatography (dichloromethane:methanol=97:3) to yield the compound of interest (122 mg, 39%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.42 (s, 2H), 6.93 (d, 1H J=8.0 Hz), 5.58 (s, 1H), 5.29 (m, 2H), 5.21 (s, 1H), 4.29 (s, 2H), 4.26 (s, 2H), 4.06 (m, 1H), 3.97 (s, 2H), 2.17-1.58 (m, 13H).

Provenance & Evidence