Diethylamine → HCID 11663641, compound

Participants

Reaction Steps

To a solution of {2-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)propionylamino]-thiazol-5-ylsulfanyl}-acetic acid (33 mg, 70.4 mmol) in DMF (0.5 mL) was added 3-hydroxy-1,2,3-benzotriazin-4-(3H)-one (12 mg, 73.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (14 mg, 73 mmol). The reaction mixture was stirred at room temperature for 2 hours after which diethyl amine (10 μL, 96.3 mmol) and DIPEA (12 μL, 70.3 mmol) were added. Stirring was continued for 20 hours. The reaction mixture was purified by HPLC (C18, gradient 25%-100% acetonitrile) to give 3-cyclopentyl-N-(5-diethylcarbamoylmethylsulfanyl-thiazol-2-yl)-2-(4-methanesulfonyl-phenyl)propionamide as an oil. Yield: 15 mg (42%). 1H-NMR (CDCl3): δ 7.91 (d, 2H), 7.62 (d, 2H), 7.45 (s, 1H), 3.93 (t, 1H), 3.63 (s, 3H), 3.38 (q, 2H), 3.31 (q, 2H), 3.05 (s, 3H), 2.28-2.21 (m, 1H), 1.97-1.90 (m, 1H), 1.75-1.47 (m, 7H), 1.23-1.11 (m, 8H); HPLC-MS: m/z: 525 (M+1).

Provenance & Evidence