Hydrochloric Acid → 1-[5-[2-(Ethylcarbamoylamino)-7-(2-methoxyethoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(2-methoxyethoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (86 mg, 0.141 mmol) was dissolved in EtOH (15 mL) and 2M aqueous NaOH (5 mL) added. The reaction was then stirred at 70° C. for 2 h then cooled to rt, 2M HCl (10 mL) was added and the mixture was stirred for 1 h. The mixture was then extracted with EtOAc (3×25 mL) and the combined organic fractions, washed with brine, separated, dried (Na2SO4) and concentrated under reduced pressure to afford Compound 202 (60 mg, 81%) as an off-white solid. 1H NMR (DMSO-d6): δ=12.40 (bs, 1H), 10.76 (bs, 1H), 8.75 (s, 2H), 7.82 (d, J=1.5 Hz, 1H), 7.41 (d, J=1.4 Hz, 1H), 6.84 (bt, J=5.4 Hz, 1H), 4.68 (s, 2H), 4.28 (dt, J=13.8 and 4.2 Hz, 2H), 3.39-3.30 (m, 2H), 3.35 (s, 3H), 3.25-3.17 (m, 2H), 2.05-2.00 (m, 2H), 1.39 (ddd, J=13.8, 10.2 and 3.9 Hz, 2H), 1.20 (s, 3H), 1.12 (t, J=7.2 Hz, 3H). MS: 529.16 [M+H]+.

Provenance & Evidence