Water → HCID 86664013, compound

Participants

Reaction Steps

To an ice-cold solution of ethyl 4-allyl-1-(5-(2-(3-ethylureido)-7-(pyrazin-2-yl)benzothiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate (0.26 g, 0.45 mmol) in DMSO (2.0 mL) was added potassium tert-butoxide (0.25 g, 2.25 mmol). The resulting mixture was stirred at rt for 2 h. After completion of reaction (by TLC), water (10 mL) was added followed by extraction with EtOAc (2×50 mL). The organic layer was discarded and the pH of the aqueous layer was adjusted up to 4-5, then extracted with hot EtOAc (3×100 mL) and the combined organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with ether to afford Compound 139 as a beige solid (0.13 g, 53% yield). 1H NMR (DMSO-d6): δ 1.09 (t, J=7.20 Hz, 3H), 1.44 (m, 2H), 2.05 (m, 2H), 2.29 (m, 2H), 3.17-3.22 (m, 4H), 4.43 (m, 2H), 5.07 (m, 2H), 5.71 (m, 1H), 6.90 (br s, 1H), 8.03 (s, 1H), 8.40 (s, 1H), 8.69 (d, J=2.80 Hz, 1H), 8.87 (d, J=2.0 Hz, 1H), 8.94 (s, 2H), 9.77 (s, 1H), 10.71 (br s, 1H) and 12.69 (br s, 1H). MS: 545.26 [M+H]+.

Provenance & Evidence