Pyridine → HCID 56963343, compound

Participants

Reaction Steps

To a solution of 6-[3-aminopropyl(methylsulfonyl)amino]-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-indazole-3-carboxamide (i) (5 mg, 0.01 mmol) in DCM (0.5 mL) at 0° C. was added pyridine (50 μL) followed by cyclobutanecarbonyl chloride (3 μL, 0.026 mmol). The mixture was then stirred at RT for 16 h. More pyridine (20 μL) and cyclobutylcarbonyl chloride (10 μL) were added and the mixture was left to stir for another 5 h. The solvent was then evaporated under reduced pressure. The residue was taken up in EtOAc (2 mL), washed with saturated aqueous sodium bicarbonate solution (1 mL), dried (MgSO4) and concentrated in vacuo. The crude material was purified by preparative LCMS (5-40-70-100% ACN in 0.1% aqueous formic acid) to afford Compound (62) as a white solid (2.5 mg, 43%). ESI-MS m/z calculated for [M+H]+: 602.1/604.1; found: 601.9/603.9; 1H NMR (400 MHz, CDCl3) δ 7.74 (s, 1H), 7.71-7.60 (m, 2H), 7.50-7.41 (m, 2H), 7.36 (s, 1H), 5.82 (t, J=6.0 Hz, 2H), 3.92-3.65 (m, 2H), 3.55-3.26 (m, 2H), 3.04 (d, J=11.1 Hz, 3H), 3.02-2.90 (m, 4H), 2.44-2.30 (m, 1H), 2.30-2.07 (m, 4H), 2.03-1.81 (m, 2H), 1.77 (p, J=6.6 Hz, 2H), 1.17-0.94 (m, 3H), 0.72-0.52 (m, 1H).

Provenance & Evidence