Lithium Hydroxide → 1-[5-[2-(Ethylcarbamoylamino)-7-(4-methyl-2-pyridyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of ethyl 1-(5-(2-(3-ethylureido)-7-(4-methylpyridin-2-yl)benzothiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate (0.015 g, 0.026 mmol) in THF was added aqueous LiOH (0.006 g, 0.134 mmol dissolved in minimum amount of H2O) and the mixture heated up to 65° C. for 3 h. After reaction completion (by TLC), the solvent was concentrated and 10 mL of water added and washed with EtOAc (2×50 mL). The organic layer was discarded and the pH of the aqueous layer was adjusted up to 4-5 then extracted with hot EtOAc (3×50 mL) and the combined organic layer dried over Na2SO4 and solvent evaporated under reduced pressure. The residue thus obtained was triturated with ether to afford the desired product as an off-white solid (0.005 g, 35%). 1H NMR (DMSO-d6): δ 1.11 (t, J=7.20 Hz, 3H), 1.19 (s, 3H), 1.41 (m, 2H), 2.07 (m, 2H), 2.45 (s, 3H), 3.17-3.24 (m, 4H), 4.32 (m, 2H), 6.93 (br s, 1H), 7.27 (d, J=4.80, 1H), 7.94 (s, 1H), 8.23 (s, 1H), 8.35 (s, 1H), 8.65 (d, J=4.8 Hz, 1H), 8.91 (s, 2H) and 10.60 (br s, 1H). MS: 530.21 [M−H]−.

Provenance & Evidence