Diisopropylethylamine → 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid-[(R)-1-(3,4-diethyl-benzyl)-2-(4-dimethylamino-piperidin-1-yl)-2-oxo-ethyl]-amide

Participants

Reaction Steps

A mixture of 400 mg (0.81 mmol) (R)-3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid, 280 mg (0.87 mmol) TBTU, 0.17 mL (0.97 mmol) ethyldiisopropylamine and 45 mL THF was stirred for 1 h at RT, then combined with 130 mg (1.01 mmol) dimethyl-piperidin-4-yl-amine and 5 mL DMF and stirred overnight. The reaction mixture was diluted by the addition of 30 mL EtOAc, extracted with 30 mL of a 15% K2CO3 solution and the organic phase was dried. The product fractions were evaporated down under reduced pressure, the residue was triturated with diisopropylether, suction filtered and dried.

Provenance & Evidence