Triethylamine → 3-(2-Chlorophenyl)-N-[4-chloro-3-[(1H-pyrrolo[2,3-b]pyridin-5-ylamino)carbonyl]phenyl]-5-isoxazolecarboxamide

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Reaction Steps

2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) (0.084 g, 0.26 mmol) and triethylamine (50 μL, 0.35 mmol) were added to a solution of 3-(2-chloro-phenyl)-2,3-dihydro-isoxazole-5-carboxylic acid (0.058 g, 0.26 mmol) in DMF (1 ml) and the reaction stirred for 10 minutes at room temperature. 5-Amino-2-chloro-N-(1H-pyrrolo[2,3-b]pyridin-5-yl)-benzamide (0.050 g, 0.175 mmol) was added to the reaction mixture and stirred for a further 24 hours. The solvent was removed under reduced pressure then methanol (3 ml) and ammonium hydroxide (1 ml) were added to the residue and the mixture stirred for a further 3 hours. The solvent was removed under reduced pressure and the resultant solid triturated with acetonitrile:water (1:1, 5 ml). The solid was filtered to afford 3-(2-Chloro-phenyl)-isoxazole-5-carboxylic acid [4-chloro-3-(1H-pyrrolo[2,3-b]pyridin-5-ylcarbamoyl)-phenyl]-amide 0.033 g (37% yield)

Provenance & Evidence