Sodium Hydroxide → HCID 57731467, compound

Participants

Reaction Steps

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (49.9 mg, 0.13 mmol) was added to a solution of 2-methoxycarbonylamino-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid (75 mg, 0.13 mmol), pyrrolidine (9.33, 0.13 mmol) and di-iso-propyl ethyl amine (51 mg, 0.39 mmol) in N,N-Dimethylformamide (1 ml). The reaction was stirred at room temperature for 1 hour, then methanol (2 ml) was added followed by aqueous sodium hydroxide (0.2 ml) and the reaction was stirred at room temperature for 16 hours. This solution was then neutralized with acetic acid and the compound was purified by preparative mass-triggered reverse-phase HPLC chromatography to give [4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-(pyrrolidine-1-carbonyl)-phenyl]-carbamic acid methyl ester as a white solid.). 1H NMR (500 MHz, DMSO-d6) δ 1.81 (p, J=6 Hz 1H); 1.87 (p, J=6 Hz 1H); 3.41 (t, J=6 Hz 1H); 3.48 (t, J=6 Hz 1H); 3.65 (s, 3H); 3.81 (s, 3H); 7.04 (t, J=8 Hz 1H) 7.13 (d, J=8 Hz 1H); 7.29 (t, J=8 Hz, 1H); 7.60 (d, J=8 Hz 1H); 7.75 (m, 4H); 8.17 (s, 1H); 8.55 (s, 1H); 9.23 (s, br, 1H); 11.95 (s, br, 1H) (21.8 mg, 36% yield MS: m/z 471.5 (M+H+).

Provenance & Evidence