2-(Methylamino)ethanol → HCID 57731569, compound

Participants

Reaction Steps

To a solution of 3-Fluoro-2-(4-hydroxy-cyclohexylamino)-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid (63 mg, 0.1 mmol) in anhydrous THF (1 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (57 mg, 0.15 mmol), diisopropylethylamine (52 μL, 0.3 mmol), and 2-methylaminoethanol (11 mg, 0.15 mmol). The reaction solution was irradiated in a Personal Chemistry Optimizer at 100° C. for 2 min and 200 μL of 50% w/v aqueous potassium hydroxide was added. The mixture was stirred for 15 h and 100 μL of glacial acetic acid was added. The suspension was dissolved in DMSO and water and directly purified by reverse-phase HPLC to afford the title compound as a white powder (5 mg, 0.009 mmol, 9% yield). 1H-NMR (500 MHz, d6-DMSO, 70° C.) δ=8.48 (d, J=2 Hz, 1H), 8.11 (d, J=2.0 Hz, 1H), 7.67 (s, 1H), 7.60 (dd, J=7 Hz, J2=2 Hz, 1H), 7.47 (dd, J1=14 Hz, J2=2.0 Hz, 1H), 7.28 (m, 1H), 7.22 (m, 1H), 7.12 (d, J=8.0 Hz, 1H), 7.05 (t, J=8.0 Hz, 1H), 4.55 (m, 1H), 3.99 (m, 1H), 3.82 (s, 3H), 3.11 (m, 1H), 2.97 (s, 3H), 2.9 (m, 3H), 2.76 (m, 2H), 2.66 (m, 2H), 1.92 (m, 4H), 1.56 (m, 4H); MS: m/z 533 [MH+].

Provenance & Evidence