Water → 1-(5-(2-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-yl)pyridazin-3-yl)-4-methylpiperidine-4-carboxylic acid

Participants

Reaction Steps

To an ice-cold solution of ethyl 1-(5-(2-(3-ethylureido)-7-(pyridin-2-yl)benzo[d]thiazol-5-yl)pyridazin-3-yl)-4-methylpiperidine-4-carboxylate (0.05 g, 0.092 mmol) in DMSO (2 mL) was added potassium tert-butoxide (0.051 g, 0.45 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 (3×50 mL) and the organic layer discarded. The pH of the aqueous layer was adjusted up to 4-5, extracted with EtOAc (3×50 mL) and the combined organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with ether to obtain Compound 195 as an off-white solid (0.025 g, 53%). 1H NMR (DMSO-d6): δ 9.15 (s, 1H), 8.82 (m, 1H), 8.55 (d, J=8.0 Hz, 1H), 8.38 (s, 1H), 8.21 (s, 1H), 8.02 (t, J=8.0 Hz, 1H), 7.90 (m, 1H), 7.64 (s, 1H), 7.46 (m, 1H), 7.17 (br s, 1H), 4.20 (m, 2H), 3.19-3.24 (m, 4H), 2.10 (m, 2H), 1.43 (m, 2H), 1.22 (s, 3H) and 1.01 (t, J=7.2 Hz, 3H). MS: 518.29 [M+H]+.

Provenance & Evidence