Methanol → HCID 86664035, compound

Participants

Reaction Steps

Ethyl-4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate (1.75 g, 3.43 mmol) was dissolved in THF (60 mL) and MeOH (125 mL) and an aqueous solution of KOH (125 mL; 1 mol/L) was introduced and refluxed overnight. After this period the mixture was diluted with water (150 mL), washed with Et2O/EtOAc (1:1, 100 mL) and the residual aqueous acidified to pH 1 (3M HCl) and back extracted with EtOAc (3×100 mL). The organic fractions were combined, dried (MgSO4) and concentrated in vacuo affording 1.05 g (64% yield) of the product as a light yellow solid after flash column chromatography on silica gel (0-10% DCM/MeOH). 1HNMR (CDCl3): δ 10.16 (s, 1H), 8.56 (d, J=20.7 Hz, 2H), 7.95 (d, J=1.5 Hz, 1H), 7.81 (d, J=1.6 Hz, 1H), 4.51 (d, J=13.9 Hz, 2H), 3.39-3.32 (m, 2H), 3.26-3.15 (m, 2H), 2.20 (d, J=13.4 Hz, 2H), 1.59 (q, J=7.5 Hz, 2H), 1.48-1.34 (m, 2H), 1.21 (t, J=7.2 Hz, 3H), 0.87 (t, J=7.5 Hz, 3H). MS: 483.1 [M+H]+.

Provenance & Evidence