Dimethylamine → Trifluoroacetic acid

Participants

Reaction Steps

To a flask containing the title compound from Example 54 Step A (10 mg, 0.03 mmol) and O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (13 mg, 0.034 mmol) in N,N-dimethylformamide (290 μL) was added a solution of dimethylamine in tetrahydrofuran (2 M, 17 μL, 0.034 mmol) followed by diisopropylethylamine (25 μL, 0.14 mmol). The reaction was stirred at room temperature overnight. The reaction was then acidified with trifluoroacetic acid, passed through a syringe filter and purified by HPLC (C18 column, 10 to 100% acetonitrile/water, both 0.1% v/v trifluoroacetic acid) to afford the title compound: LCMS m/z 376.06 [M+H]+; 1H NMR (500 MHz, CDCl3) 8.76 (s, 1H), 8.57 (s, 1H), 7.69 (s, 1H), 7.61-7.57 (m, 3H), 3.20-3.17 (m, 2H), 3.12-3.09 (m, 2H), 2.97 (br s, 3H), 2.81 (s, 3H), 2.59 (br s, 3H), 1.65 (s, 6H).

Provenance & Evidence