1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 89926841, compound

Participants

Reaction Steps

To adamantyl amine hydrochloride (74 mg, 0.32 mmol) in DMSO (800 mg), were successively added DIPEA (208 mg, 1.60 mmol), i-PrOH (25 mL), 2-(6-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-methyl-1,1-dioxido-1,2,6-thiadiazinan-2-yl) acetic acid (160 mg, 0.38 mmol), EDCI (123 mg, 0.64 mmol) and HOBt monohydrate (124 mg, 0.64 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 (113 mg, 49%, white solid). 1H NMR (300 MHz, CDCl3): δ 7.69 (s, 1H), 7.65 (s, 1H), 6.95 (d, 1H, J=6.8 Hz), 5.58 (s, 1H), 5.29 (s, 1H), 4.40-4.34 (m, 1H), 4.12-3.90 (m, 3H), 3.78-3.72 (m, 1H), 3.33-3.21 (m, 2H), 2.62-2.59 (m, 1H), 2.14-1.58 (m, 13H), 0.97 (d, 3H, J=6.0 Hz). LC/MS MH+ 597

Provenance & Evidence