Triethylamine → HCID 67282546, compound

Participants

Reaction Steps

5-(4-Aminopiperidin-1-yl)-7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (15 mg, 0.034 mmol) was dissolved in anhydrous N,N-dimethylformamide (0.3 mL), and Boc-glycine (7 mg, 0.037 mmol), and then 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (8 mg, 0.04 mmol), 1-hydroxybenztriazole (5 mg, 0.04 mmol), and triethylamine (6 μL, 0.04 mmol) were added. The reaction was stirred at ambient temperature for 24 hours. The solution was diluted with ethyl acetate (5 mL), washed with saturated sodium bicarbonate (3×1 mL), dried with sodium sulfate, decanted and concentrated in vacuo. Column chromatography eluting with a gradient of 70-100% ethyl acetate in hexanes provided tert-butyl 2-(1-(7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)piperidin-4-ylamino)-2-oxoethylcarbamate (3 mg, 15%). This material was dissolved in dichloromethane (0.2 mL) and trifluoroacetic acid (0.1 mL) and stirred at ambient temperature for 1 hour then concentrate in vacuo. Azeotroping four times with dichloromethane provided 2-amino-N-(1-(7-chloro-1-methyl-3-(naphthalen-2-ylmethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)piperidin-4-yl)acetamide as the trifluoroacetate salt (3 mg, quant. yield). ESI m/z measured 504.2173 [M+H]+. calculated 504.2166.

Provenance & Evidence