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

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Reaction Steps

Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(pyrimidine-2-carbonylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (100 mg, 0.17 mmol) was dissolved in DMSO (0.5 mL) with stirring and potassium-t-butoxide (40 mg, 0.35 mmol) added. The reaction was allowed to stir at rt for 2 h. The reaction mixture was filtered and purified by preparative HPLC to afford Compound 146 as a solid (5 mg). 1H NMR (DMSO-d6): δ 11.01 (1H, s), 9.12 (2H, d, J=4.86 Hz), 8.77 (2H, s), 7.83 (1H, d, J=4.75 Hz), 7.82 (1H, t, J=1.44 Hz), 7.67 (1H, d, J=1.66 Hz), 7.01 (1H, s), 4.32 (2H, d, J=13.32 Hz), 3.22 (2H, p, J=7.59 Hz), 2.05 (2H, dd, J=13.04, 4.48 Hz), 1.42 (2H, t, J=11.27 Hz), 1.22 (3H, s), 1.13 (3H, dd, J=7.16, 7.16 Hz). MS: 562 [M+H]+.

Provenance & Evidence