Dichloromethane → HCID 86664041, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-[5-[7-[3-(1,3-dioxoisoindolin-2-yl)oxyprop-1-ynyl]-2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethyl-piperidine-4-carboxylate (233 mg, 0.32 mmol) was suspended in EtOH (20 mL) and sodium hydroxide solution (10 mL, 1 M, aq) was added to give a light yellow solution. The solution was heated at 100° C. then cooled to rt after 48 h. The mixture was concentrated to dryness under reduced pressure and remaining water azeotroped with MeCN. The resulting yellow residue was suspended in MeOH with sonication and warming then filtered through a PTFE filter cup. A white (salt-like) solid was obtained (discarded) and a yellow filtrate. The yellow filtrate was concentrated to dryness under reduced pressure to give a yellow solid which was suspended in water, sonicated, DCM added and the mixture filtered through a PTFE filter cup leaving a pale yellow solid. This solid was dissolved in MeOH, passed through the filter cup and the solution concentrated to dryness under reduced pressure to give a pale yellow solid which was purified by chromatography, Biotage SP4, 40 g Si cartridge, 0-5% MeOH in DCM. The relevant fractions were combined to afford Compound 197 as a pale yellow solid, 9 mg. 1H NMR (MeOD): δ 8.67 (2H, s), 7.85 (1H, d, J=1.6 Hz), 7.51 (1H, d, J=1.6 Hz), 4.57 (2H, t, J=10.2 Hz), 4.57 (2H, m), 3.60 (2H, t, J=10.2 Hz), 3.36 (2H, q, J=7.2 Hz), 3.24 (2H, m), 2.22 (2H, dm, J=13.4 Hz), 1.64 (2H, J=7.5 Hz), 1.45 (2H, m), 1.24 (3H, t, J=7.2 Hz), 0.93 (3H, t, J=7.5 Hz). MS: 524.14 [M+H]+.

Provenance & Evidence