Water → HCID 56953308, compound

Participants

Reaction Steps

To an ice-cold solution of ethyl 1-(5-(2-(3-ethylureido)-7-(pyridin-2-yl)benzothiazol-5-yl)pyrimidin-2-yl)-4-(trifluoromethyl)piperidine-4-carboxylate (0.05 g, 0.08 mmol) in DMSO (2.0 mL) was added potassium tert-butoxide (0.046 g, 0.41 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) and the organic layer discarded. The pH of the aqueous layer was adjusted up to 4-5 then extracted with hot EtOAc (3×75 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 142 as off-white solid (0.04 g, 84% yield). 1H NMR (DMSO-d6): δ 1.09 (t, J=7.20 Hz, 3H), 1.65 (m, 2H), 2.31 (m, 2H), 3.01 (m, 2H), 3.20 (q, J=7.20 Hz, 2H), 4.75 (m, 2H), 6.87 (br s, 1H, D2O exchangeable), 7.43 (m, 1H), 7.99 (m, 2H), 8.23 (s, 1H), 8.48 (d, J=7.20 Hz, 1H), 8.80 (d, J=3.60 Hz, 1H), 8.92 (s, 2H), 10.57 (br s, 1H, D2O exchangeable) and 14.06 (br s, 1H, D2O exchangeable). MS: 572.10 [M+H]+.

Provenance & Evidence