Dimethylamine → HCID 59825046, 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 hydroxy-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-acetic acid (75 mg, 0.14 mmol), dimethyl amine (2 M solution 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. Methanol (2 ml) was then added to the solution followed by 50% w/v aqueous sodium hydroxide (200 μl) and stirred at room temperature for 2 hours. The reaction was then neutralized with acetic acid and purified by preparative high pressure liquid chromatography, to give 2-hydroxy-2-{6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-acetamide (9.2 mg, 16% yield). 1H NMR (500 MHz, Dimethyl sulfoxide-d6) δ 2.86 (s, 3H) 3.32 (s, 3H); 3.82 (s, 3H)); 5.61 (m, 2H); 7.06 (t, J=8 Hz 1H); 7.15 (d, J=8 Hz, 1H) 7.31 (t, J=8 Hz, 1H); 7.44 (d, J=7.5 Hz 1H); 7.58 (d, J=8 Hz 1H); 7.73 (s, 1H); 7.58 (t, J=7.5 Hz 1H); 7.95 (d, J=7.5 Hz 1H); 7.94 (s, 1H); 8.60 (s, 1H); 8.95 (s, 1H); 11.98 (s, br, 1H) MS: m/z 403.4 (M+H+).

Provenance & Evidence