Water → N-(5-benzyl-1,2-oxazol-3-yl)-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

Participants

Reaction Conditions

Reaction Steps

A 0.5-2 mL microwave reactor vial is charged with a mixture of 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 100 mg, 0.41 mmol) and 5-benzyl-3-aminoisoxazole (107 mg, 0.61 mmol) in pyridine (500 μL) and the vial is sealed with a Teflon lined septa cap. The mixture is cooled to 0° C. and phosphorous oxychloride (40 μL, 0.43 mmol) is added. The mixture is allowed to warm to room temperature and is then irradiated in a microwave reactor at 150° C. for 60 min. The mixture is poured into water and the resulting solid is collected by filtration and is purified via preparative HPLC using a gradient elution from 10-75% acetonitrile/water with 0.1% TFA to obtain the title compound (87 mg, 53%). LCMS: 401.20 (M+H+). (System V1)

Provenance & Evidence