Potassium tert-butoxide → 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methylcarbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylic acid

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Reaction Steps

Potassium tertiary butoxide (71 mg, 0.63 mmol) was added to a solution of ethyl 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-[(E)-N-methoxy-C-methyl-carbonimidoyl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate (87 mg, 0.16 mmol) 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 116 as a white solid, 27 mg, 25% yield. 1H NMR (DMSO-d6): δ 12.49 (1H, s), 10.66 (1H, s), 8.85 (2H, s), 7.95 (1H, d, J=1.58 Hz), 7.76 (1H, d, J=1.64 Hz), 6.94 (1H, t, J=5.58 Hz), 4.49 (2H, dt, J=13.57, 3.98 Hz), 4.10 (3H, s), 3.30-3.15 (4H, m), 2.42 (3H, s), 2.10 (2H, dt, J=13.97, 2.91 Hz), 1.57 (2H, q, J=7.49 Hz), 1.38 (2H, ddd, J=13.34, 11.14, 4.02 Hz), 1.14 (3H, t, J=7.17 Hz), 0.85 (3H, t, J=7.43 Hz). MS: 526 [M+H]+.

Provenance & Evidence