Potassium tert-butoxide → 1-[5-[2-(Ethylcarbamoylamino)-7-[2-(3-methylimidazol-4-yl)ethynyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid

Participants

Reaction Steps

Potassium tertiary butoxide (150 mg, 1.35 mmol) was added to a solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[2-(3-methylimidazol-4-yl)ethynyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate in DMSO (1.5 mL). The mixture was stirred at rt for 2 h after which time LCMS indicated clean conversion to the acid. The mixture was filtered through cotton wool to remove solid particulates and purified by preparative-HPLC to give Compound 144 as a white solid, 43 mg, 29% yield for 2 steps. 1H NMR δ (ppm) (DMSO-d6): 8.81 (2H, s), 7.95 (1H, d, J=1.55 Hz), 7.89 (1H, s), 7.73 (1H, d, J=1.56 Hz), 7.45 (1H, s), 7.27 (1H, t, J=5.58 Hz), 4.32 (2H, dt, J=13.70, 4.46 Hz), 3.83 (3H, s), 3.37 (2H, ddd, J=14.10, 10.43, 4.06 Hz), 3.23 (2H, p, J=6.90 Hz), 2.06 (2H, dt, J=13.39, 3.62 Hz), 1.41 (2H, ddd, J=13.36, 10.05, 3.86 Hz), 1.21 (3H, s), 1.13 (3H, t, J=7.15 Hz). MS: 545 [M+H]+.

Provenance & Evidence