Sodium Hydroxide → HCID 86664048, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-ethyl-1-[5-[2-(ethylcarbamoylamino)-7-(methoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate (23 mg, 0.042 mmol) was dissolved in EtOH (1 mL) and 2M aqueous NaOH (330 μL, 0.66 mmol) added. The reaction mixture was stirred at 70° C. for 15 mins before additional 2M NaOH (670 μL, 1.34 mmol) was added and the reaction continued for 1.5 h then temperature increased to 100° C. and reaction continued for 4 h after which time the reaction was allowed to cool to rt overnight. After this time LCMS indicated small amount of starting material still present and the reaction was completed by heating to 100° C. for a further 2 h after which time the reaction was cooled to rt, diluted with water and extracted with DCM (3×). The aqueous layer was acidified with 10% HCl (aq) before extracting with EtOAc (3×) and the combined EtOAc extracts dried and the solvent evaporated to yield the Compound 203 (13.5 mg, 64%). 1H NMR (MeOD) δ 8.54 (s, 2H), 7.66 (bd, J=1.4 Hz, 1H), 7.28 (s, 1H), 4.68 (s, 2H), 4.48 (dt, J=13.7, 3.6 Hz, 2H), 3.35-3.28 (m, 2H), 3.22-3.11 (m, 2H), 2.20-2.13 (m, 2H), 1.60 (q, J=7.5 Hz, 2H), 1.44-1.34 (m, 2H), 1.21 (t, J=7.2 Hz, 3H), 0.89 (t, J=7.5 Hz, 3H). MS: 499.12 [M+H]+

Provenance & Evidence