Potassium tert-butoxide → HCID 56953212, compound

Participants

Reaction Steps

Potassium tert butoxide (67 mg, 0.59 mmol) was added to a solution of ethyl 1-[5-[7-(ethylcarbamoyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (78 mg, 0.147 mmol) in DMSO (1.5 mL). The mixture was stirred at ambient temperature 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. Compound 97 was obtained as a white solid, 44 mg, 75% yield. 1H NMR (DMSO-d6): δ 10.86 (1H, s), 8.88 (2H, s), 8.82 (1H, t, J=5.47 Hz), 8.12 (1H, d, J=1.57 Hz), 8.05 (1H, d, J=1.45 Hz), 7.14 (1H, t, J=5.61 Hz), 4.32 (2H, dt, J=13.66, 4.46 Hz), 3.24 (5H, p, J=6.88 Hz), 3.20-3.27 (2H, m), 2.06 (2H, dt, J=13.52, 3.72 Hz), 1.41 (2H, ddd, J=13.42, 10.06, 3.89 Hz), 1.24 (1H, s), 1.22 (3H, t, J=3.29 Hz), 1.21 (3H, s), 1.14 (3H, t, J=7.17 Hz). MS: 512 [M+H]+.

Provenance & Evidence