Acetic Acid → HCID 57731483, compound

Participants

Reaction Steps

Into a 5 mL screw-cap vial were added 2,3-Difluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide (100 mg, 0.178 mmol) and 1-methyl-piperidin-4-ylamine (102 mg, 0.712 mmol). The vial was sealed and placed in heated block at 120° C. for 48 h. The reaction solution was dissolved in 1:1 methanol/acetone (2 mL total) and treated with 100 μL of 50% w/w aqueous potassium hydroxide for 1 h. Glacial Acetic acid was added to obtain pH 7, then the reaction mixture was concentrated. The residue was purified by reverse-phase HPLC to afford the title compound as a white powder (4 mg, 0.008 mmol, 4% yield). 1H-NMR (500 MHz, d6-DMSO) δ=11.87 (d, J=2 Hz, 1H), 8.49 (d, J=2.5 Hz, 1H), 8.12 (d, J=2.0 Hz, 1H), 7.71 (d, J=2.5 Hz, 1H), 7.61 (dd, J1=8.0 Hz, J2=2.0 Hz, 1H), 7.54 (dd, J=13.5 Hz, J2=2.0 Hz, 1H), 7.24-7.3 (m, 2H), 7.12 (dd, J1=8.5 Hz, J2=1.0 Hz, 1H), 7.04 (td, J1=7.5 Hz, J2=1.0 Hz, 1H), 4.57 (dd, J1=5 Hz, J2=2.5 Hz, 1H), 3.81 (s, 3H), 3.14 (m, 1H), 3.00 (s, 3H), 2.9 (s, 3H), 3.14 (m, 1H), 2.12 (s, 3H), 1.87 (m, 2H), 1.74 (m, 2H), 1.41 (m, 2H); MS: m/z 502 [MH+].

Provenance & Evidence