Sodium Hydroxide → 4-Ethyl-1-(5-(2-(3-ethylureido)-7-propionylbenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-ethyl-1-(5-(2-(3-ethylureido)-7-propionylbenzo[d]thiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylate (0.025 g, 0.046 mmol) in EtOH (5 mL) was added an aqueous solution (1 mL) of NaOH (0.0092 g, 0.232 mmol) and the mixture stirred overnight at 80° C. After reaction completion (by TLC), the EtOH was evaporated under reduced pressure, water (10 mL) was added to the residue and extracted with EtOAc (3×25 mL) and the organic layers discarded. The aqueous layer was acidified to pH 4-5 with 1N HCl, extracted with EtOAc (3×25 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4, filtered then concentrated under reduced pressure. The residue was purified by preparative TLC (5% MeOH in DCM) to obtain Compound 207 as white solid (0.007 g, 30%). 1H NMR (DMSO-d6): δ 10.82 (br s, 1H), 8.86 (s, 2H), 8.23 (s, 1H), 8.14 (s, 1H), 6.95 (br s, 1H), 4.46 (m, 2H), 3.36 (m, 2H), 3.13-3.24 (m, 4H), 2.08 (m, 2H), 1.51-1.53 (m, 2H), 1.32 (m, 2H), 1.16 (t, J=7.2 Hz, 3H), 1.10 (t, J=7.2 Hz, 3H) and 0.81 (t, J=7.2 Hz, 3H). MS: 511.24 [M+H]+.

Provenance & Evidence