Dimethylamine → HCID 178489385, compound

Participants

Reaction Steps

In a microwave vial O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (53.9 mg, 0.14 mmol) was added to a solution of 5-hydroxy-{6-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxylethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-pyridin-2-yl}-acetic acid (71 mg, 0.14 mmol), dimethyl amine (2 M in THF, 65 μl, 0.14 mmol) and di-iso-propyl ethyl amine (75 μl, 0.43 mmol) in tetrahydrofuran (1 ml). The vial was sealed and the solution irradiated to 70° C. for 10 min in a microwave reactor. The solvent was then removed under reduced pressure and 1 ml of trifluoroacetic acid was added this reaction was stirred for 16 hours and the solvent evaporated under reduced pressure, and purified by preparative mass-triggered reverse-phase HPLC to afford 2-hydroxy-2-{6-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-acetamide (13.6 mg, 24% yield). 1H NMR (500 MHz, Dimethyl sulfoxide-d6) δ 2.85 (s, 3H) 3.30 (s, 3H); 3.85 (s, 3H)); 5.63 (m, 2H); 7.10 (t, J=8 Hz 1H); 7.4 (d, J=8 Hz 1H); 7.44 (m, 2H); 7.63 (d, J=8 Hz 1H); 7.87 (m, 2H) 8.88 (s, 1H); 9.22 (s, 1H); 13.84 (s, br, 1H) MS: m/z 404.3 (M+H+).

Provenance & Evidence