Hexane → 1-[5-[2-(Ethylcarbamoylamino)-7-[2-(6-methoxy-2-pyridyl)ethynyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid (0.18 g, 0.39 mmol) in DMF (5 mL) was added 2-bromo-6-methoxy pyridine (0.15 g, 0.77 mmol) and DIPEA (0.16 mL, 1.16 mmol). The reaction mass was degassed by purging N2 for 15 min followed by addition of CuI (0.015 g, 0.077 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.067 g, 0.058 mmol). The reaction mixture was again degassed for 10-15 min then heated up to 80° C. for 30 min under microwave irradiation. The mixture was then poured in 100 mL of ice-cold water, extracted with EtOAc (3×100 mL) and the combined organic layer washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 30% EtOAc:hexane to obtain Compound 152 as an off-white solid (0.01 g, 5% yield). 1H NMR (DMSO-d6): δ 1.09 (t, J=7.20 Hz, 3H), 1.19 (s, 3H), 1.41 (m, 2H), 2.02 (m, 2H), 3.19 (m, 2H), 3.30 (m, 2H), 3.90 (s, 3H), 4.30 (m, 2H), 6.77 (br s, 1H), 6.93 (d, J=8.40 Hz, 1H), 7.34 (d, J=7.20 Hz, 1H), 7.66-7.82 (m, 2H), 7.97 (s, 1H), 8.81 (s, 2H), 10.91 (br s, 1H) and 12.46 (br s, 1H). MS: 572.05 [M+H]+.

Provenance & Evidence