Hydrochloric Acid → HCID 86664057, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (192 mg, 0.349 mmol) was dissolved in EtOH (20 mL) and 2M aqueous NaOH (10 mL) added. The reaction mixture was stirred at 70° C. for 2 h then cooled to rt and 2M HCl (20 mL) added. The mixture was extracted with hot EtOAc (3×50 mL), the aqueous phase saturated with NaCl and further extracted with EtOAc (50 mL) and the combined organic fractions washed with brine, separated, dried (Na2SO4) and concentrated under reduced pressure. The solid residue was washed with MeCN then Et2O to afford Compound 213 (163 mg, 89%) as a pale-yellow solid. 1H NMR (DMSO-d6): δ10.98 (bs, 1H), 8.81 (s, 2H), 8.11 (d, J=1.8 Hz, 1H), 8.10 (d, J=1.8 Hz, 1H), 7.06 (bt, J=5.4 Hz, 1H), 4.31 (dt, J=13.9 and 4.4 Hz, 2H), 3.37 (ddd, J=13.3, 10.2 and 2.9 Hz, 2H), 3.26-3.19 (m, 2H), 2.76 (s, 3H), 2.09-2.02 (m, 2H), 1.43 (ddd, J=13.8, 10.2 and 3.9 Hz, 2H), 1.21 (s, 3H), 1.13 (t, J=7.2 Hz, 3H). MS: 523.13 [M+H]+.

Provenance & Evidence