1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874393, compound

Participants

Reaction Steps

DIPEA (170 mg, 1.3 mmol) was added to a stirred solution of to a stirred solution of 3′-dimethylamino-biphenyl-4-carboxylic acid (80 mg, 0.33 mmol) (generated from methyl 3′-amino(1,1′-biphenyl)-4-carboxylate) in DMF (2 mL) followed by HOBt (49 mg, 0.36 mmol) and EDCI (126 mg, 0.66 mmol). After 2 minutes of stirring, 2-amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (110 mg, 0.36 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure The residue was purified by preparative HPLC to afford 36 mg (22% Yield) of 3′-dimethylamino-biphenyl-4-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 492, 86.69%. 1H NMR (300 MHz, DMSO-d6): δ 8.6 (t, 1H), 8.0-7.9 (d, 2H), 7.8-7.7 (d, 3H), 7.5-7.4 (d, 1H), 7.36-7.24 (m, 3H), 7.1-7.0 (m, 2H), 7.0-6.94 (m, 1H), 6.88-6.8 (d, 1H), 4.8 (q, 1H), 4.2 (d, 2H), 4.0-3.7 (m, 4H), 3.5 (m, 3H), 3.0 (s, 6H), 2.0-1.8 (m, 3H), 1.8-1.6 (m, 3H).

Provenance & Evidence