Pyridine → N-(5-benzyl-1,2-oxazol-3-yl)-10-methyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxamide

Participants

Reaction Steps

To a suspension of 10-methyl-6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3′,2′:4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid (Intermediate G, 75 mg, 0.29 mmol) in CH2Cl2 (5 mL) is added 1-chloro-N,N,2-trimethylpropenylamine (138 μL, 1.01 mmol) and the mixture is stirred at room temperature for 30 min. 5-benzyl-1,2-oxazol-3-amine (Intermediate W, 252 mg, 1.45 mmol) and pyridine (94 μL, 1.16 mmol) are added and the reaction is stirred at room temperature for 20 h. The mixture is concentrated under reduced pressure and the residue is purified via preparative HPLC using a gradient elution from 10-90% acetonitrile/H2O with 0.1% TFA to afford the title compound (19 mg, 16%). LCMS: 416.20 (M+H+). (System V-med polar)

Provenance & Evidence