Diisopropylethylamine → (S)-3-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-1,1-bis-[3-(3-{[(1-methyl-1H-imidazol-2-ylmethyl)-carbamoyl]-methoxy}-phenyl)-propyl]-piperidinium hydroxide

Participants

Reaction Steps

(S)-1,1-Bis-[3-(3-carboxymethoxy-phenyl)-propyl]-3-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)amino]-piperidinium chloride (100 mg, 0.13 mmol),), C-(1-Methyl-1H-imidazol-2-yl)-methylamine (53 mg, 0.29 mmol) and N,N-Diisopropylethylamine (225 μl, 1.3 mmol) are dissolved in N,N-dimethylformamide (3.5 ml), 2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (93 mg, 0.29 mmol) is added. The reaction is stirred at room temperature overnight and purified by preparative HPLC-MS (MeOH/H2O+0.1% TFA). The product is dissolved in dichloromethane, washed with a 2 molar potassiumcarbonate solution, dried over sodiumsulfate and concentrated in vacuo. LC (method L): tR=1.15 min; Mass spectrum (ESI+): m/z=841 [M]+. IC50=0.007

Provenance & Evidence