(4-Chlorophenyl)acetic acid → 2-(4-chlorophenyl)-N-[2-[[(1R)-2,3-dihydro-1H-inden-1-yl]amino]-4H-3,1-benzoxazin-5-yl]acetamide

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Reaction Steps

4-Chlorophenylacetic acid (122 mg, 0.65 mmol), N,N-diisopropyl ethyl amine (245 mg, 1.9 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (254 mg, 0.79 mmol) were dissolved in dichloromethane (5 mL) and dimethylformamide (1 mL). The reaction mixture was stirred at room temperature for 30 minutes. (R)—N2-Indan-1-yl-4H-benzo[d][1,3]oxazine-2,5-diamine (example 2) (150 mg, 0.54 mmol) was added and stirring was continued overnight. The reaction mixture was diluted with water and extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate and evaporated. The crude product was recrystallized from isopropanol and diisopropylether. The title compound (95 mg, 41%) was obtained as a white solid; MS: m/e=430.5 (M−H+).

Provenance & Evidence