Water → HCID 178465314, compound

Participants

Reaction Steps

To an ice-cold solution of ethyl 4-ethyl-1-(5-(2-(3-ethylureido)-7-(pyridin-2-yl)-1H-benzo[d]imidazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate (0.20 g, 0.37 mmol) in DMSO (3.0 mL) was added potassium tert-butoxide (0.2.06 g, 1.84 mmol) and the mixture stirred at rt for 16 h. After completion of reaction (by TLC), water (10 mL) was added followed by extraction with EtOAc (3×25 mL) and the organic layer discarded. The pH of the aqueous layer was adjusted up to 4-5, extracted with EtOAc (3×25 mL) and the combined organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with n-pentane to afford Compound 229 as yellow solid (0.10 g, 53%). 1H NMR (DMSO-d6+D2O): δ 8.78 (m, 3H), 8.38 (m, 1H), 7.95-8.0 (m, 2H), 7.69 (s, 1H), 7.39 (br s, 1H), 4.44 (m, 2H), 3.22 (m, 2H), 3.13 (m, 2H), 2.06 (m, 2H), 1.51 (m, 2H), 1.34 (m, 2H), 1.11 (t, J=7.20 Hz, 3H) and 0.80 (t, J=7.20 Hz, 3H). LCMS: 515.19 [M+H]+

Provenance & Evidence