Triethylamine → (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[1'-(2-morpholin-4-yl-ethoxycarbonyl-methyl)-4,4'-bipiperidinyl-1-yl]-2-oxo-ethyl 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Participants

Reaction Steps

A mixture of 230 mg (0.29 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-(1′-carboxymethyl-4,4′-bipiperidinyl-1-yl)-2-oxo-ethyl 4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 15.1), 113 mg (0.35 mmol) TBTU, 84 μL (0.60 mmol) triethylamine and 39.3 mg (0.30 mmol) 2-morpholin-4-yl-ethanol in 5 mL DMF was stirred overnight at RT. The reaction mixture was poured onto saturated NaHCO3 solution, the product precipitated was suction filtered and dried at 40° C. This was dissolved in 25 mL of isopropanol and precipitated as the hydrochloride salt by the addition of 0.5 M HCl in isopropanol. This was suction filtered, washed with 5 mL isopropanol and 30 mL DIPE and dried at 30° C. in the vacuum drying cupboard.

Provenance & Evidence