HCID 87222433, compound → HCID 87222515, compound

Participants

Reaction Steps

tBuOK (124 mg, 1.11 mmol) was added to a solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methyl-carbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate in DMSO (4 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 to give Compound 88 as a white solid, 76 mg, 40% yield over 2 steps. 1H NMR (DMSO-d6): δ 10.89 (1H, s), 8.85 (2H, s), 7.95 (1H, d, J=1.62 Hz), 7.76 (1H, d, J=1.69 Hz), 7.16 (1H, t, J=5.50 Hz), 4.32 (2H, dt, J=13.67, 4.40 Hz), 4.09 (3H, s), 3.38 (2H, ddd, J=13.49, 10.48, 3.40 Hz), 3.23 (2H, p, J=6.71 Hz), 2.42 (3H, s), 2.05 (2H, dt, J=13.34, 3.66 Hz), 1.41 (2H, ddd, J=13.34, 10.04, 3.92 Hz), 1.21 (3H, s), 1.14 (3H, t, J=7.15 Hz). MS: 512 [M+H]+.

Provenance & Evidence