Dimethylformamide → Ammonia

Participants

Reaction Steps

To a solution of 3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (65 mg, 0.25 mmol) (Example 15B) (rac)-1-methyl-piperidine-3-carboxylic acid-hydrocholoride salt (50 mg, 0.27 mmol) and disopropylethylamine (50 μl, 0.27 mmol) in DMF (1 ml) was added TBTU (97 mg, 0.30 mmol). The mixture was stirred at room temperature for approximately 16 hours after which 1N aqueous NaOH (1 ml) was added and the mixture stirred for a further 1 hours. The mixture was then evaporated to dryness in vacuo and the residue purified by flash column chromatography (SiO2, eluting with a gradient of DCM:MeOH (98:2) to DCM: MeOH; conc. Aq. NH3 (70:30:3) to give N-[3-(5,6-dimethoxy-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-rac-1-methyl-piperidine 3-carboxamide (20 mg) as a colourless gum (LC/MS (basic method): Rt 2.35 min, (M+H)+ 385).

Provenance & Evidence