Water → HCID 72724620, compound

Participants

Reaction Steps

To an ice-cold solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (0.18 g, 0.33 mmol) in DMSO (2 mL) was added potassium tert-butoxide (0.184 g, 1.65 mmol) and the mixture 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). The combined organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with ether to afford the desired product as off-white solid (0.11 g, 65% yield). 1H NMR (DMSO-d6): δ 1.10 (t, J=7.20 Hz, 3H), 1.19 (s, 3H), 1.40 (m, 2H), 2.04 (m, 2H), 3.22 (q, J=7.20, 2H), 3.39 (m, 2H), 4.30 (m, 2H), 6.87 (br s, 1H, D2O exchangeable), 7.44 (m, 1H), 7.92 (s, 1H), 7.99 (m, 1H), 8.18 (s, 1H), 8.42 (d, J=8.0 Hz, 1H), 8.78 (d, (J=4.40 Hz, 1H), 8.85 (s, 2H), 10.54 (br s, 1H, D2O exchangeable) and 12.45 (br s, 1H, D2O exchangeable). MS: 518.27 [M+H]+.

Provenance & Evidence