Water → HCID 86664027, compound

Participants

Reaction Steps

To a solution of ethyl 1-(5-(2-(3-ethylureido)-4-(pyridin-2-yl)thiazolo[5,4-c]pyridin-6-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate (0.050 g, 0.091 mmol) in DMSO (2.0 mL) at rt was added potassium tert-butoxide (0.052 g, 0.45 mmol) and the mixture stirred at rt for 15-20 min. After completion of reaction (by TLC), water (25 mL) was added, followed by extraction with EtOAc (3×50 mL) and the organic layer was discarded. The pH of the aqueous layer was adjusted up to 4-5, extracted with hot EtOAc (3×50 mL) and the combined organic layer washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with ether to afford Compound 162 (0.030 g, 64%). 1H NMR (DMSO-d6): δ 1.10 (t, J=7.20 Hz, 3H), 1.20 (s, 3H), 1.44 (m, 2H), 2.04 (m, 2H), 3.22 (m, 2H), 3.37 (m, 2H), 4.35 (m, 2H), 6.86 (br s, 1H), 7.53 (m, 1H), 8.05 (m, 1H), 8.16 (s, 1H), 8.80 (d, J=8.40 Hz, 1H), 8.84 (d, J=4.40 Hz, 1H), 9.26 (s, 2H), 10.93 (br s, 1H) and 12.45 (br s, 1H). MS: 519.28 [M+H]+.

Provenance & Evidence