HCID 68183220, compound → HCID 68183404, compound

Participants

Reaction Steps

To a solution of ethyl 4-[(1E)-3-[(tert-butoxycarbonyl)amino]-1-(4-chlorophenyl)prop-1-en-1-yl]-2-(morpholin-4-yl)-1,3-thiazole-5-carboxylate (0.328 g, 0.646 mmol) in ethanol (8 mL) in a Parr bottle under an atmosphere of argon was added palladium hydroxide (0.0323 g, 0.230 mmol). The flask was purged several times with argon then filled with hydrogen to 60 psi and rapidly stirred at room temperature for 3 hours. The reaction was incomplete by LCMS. An additional portion of palladium hydroxide (0.0300 g, 0.214 mmol) was added and the reaction was stirred at room temperature under 60 psi hydrogen for 16 hours. There was further progress by LCMS but still incomplete reaction, so another portion of palladium hydroxide (0.0300 g, 0.214 mmol) was added and the reaction was stirred at room temperature under 60 psi hydrogen for 3 days. The mixture was filtered through celite, the celite was washed with methanol to extract all product, and the filtrate was concentrated. The residue was purified using column chromatography on silica gel (24 g Analogix column, gradient hexane to 40% EA in hexane over 15 minutes) to give the product (0.286 g, 87%). LCMS: (AA) ES+ 510, 512. 1H NMR (300 MHz, d4-MeOH) δ: 7.40 (d, J=8.5 Hz, 2H), 7.23 (d, J=8.5 Hz, 2H), 5.02 (dd, J=8.9, 6.6 Hz, 1H), 4.24 (q, J=6.8 Hz, 2H), 3.86-3.70 (m, 4H), 3.61-3.45 (m, 4H), 3.02-2.85 (m, 2H), 2.42-2.21 (m, 1H), 2.18-2.01 (m, 1H), 1.40 (s, 9H), 1.30 (t, J=7.1 Hz, 3H).

Provenance & Evidence