Trifluoroacetic acid → (4-(3-(azetidin-3-yl)pyrazin-2-yloxy)phenyl)(1H-benzo[d]imidazol-2-yl)methanone

Participants

Reaction Steps

To a solution of tert-butyl 3-(3-(4-(1H-benzo[d]imidazole-2-carbonyl)phenoxy)pyrazin-2-yl)azetidine-1-carboxylate (175 mg, 0.371 mmol) in CH2Cl2 (1 mL) is added 2,2,2-trifluoroacetic acid (1.0 mL). The reaction was stirred at rt 1 h. The solution was concentrated and CH2Cl2 (5 mL) and saturated NaHCO3 (0.5 mL) was added. MgSO4 was added to remove water and the solution filtered and concentrated to give the crude amine as a dark green oil which was carried on to the next step without purification. (Note: An insoluble solid crashed out during the extraction, which later was identified as the desired crude amine product, which is sparingly soluble in CH2Cl2, but soluble in THF. The insoluble solid from the extraction was dissolved in THF, dried (MgSO4), concentrated, and combined with the material from aqueous extraction and carried on into the next step.

Provenance & Evidence