Citric Acid → HCID 178510422, compound

Participants

Reaction Steps

To a mixture of 4-{4-[(4-cyano-1H-imidazole-2-carbonyl)-amino]-3-cyclohex-1-enyl-phenyl}-tetrahydro-pyran-4-carboxylic acid (as prepared in Example 18, step (d), 20.0 mg, 0.0476 mmol) and triethylamine (Et3N) (7.3 μL, 0.052 mmol) in 1 mL of THF at 0° C. was added ClCO2Et (3.6 mg, 0.038 mmol). The mixture was stirred at RT for 0.5 h and NaBH4 (5.4 mg, 0.14 mmol) was added. After stirring at RT for 16 h, the mixture was treated with 30 mL of EtOAc and 10 ml of 10% citric acid. The aqueous layer was separated and extracted with EtOAc (10 mL). The combined organic layers were washed with saturated NaHCO3 aqueous solution (10 mL), H2O (10 mL) and brine (10 mL). After drying over Na2SO4 and concentrating in vacuo, the residue was purified by silica gel chromatography (1-2% MeOH/DCM) to afford the title compound (14 mg, 70%) as a white solid. 1H-NMR (1:5 CD3OD/CDCl3; 400 MHz): δ 8.24 (d, 1H, J=8.6 Hz), 7.72 (s, 1H), 7.26 (dd, 1H, J=8.6, 2.3 Hz), 7.14 (d, 1H, J=2.3 Hz), 5.84 (m, 1H), 3.82 (m, 2H), 3.57 (s, 2H), 3.54-3.60 (m, 2H), 2.27 (m, 4H), 2.14 (m, 2H), 1.95 (m, 2H), 1.82 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C23H26N4O3, 407.2 (M+H). found 407.1.

Provenance & Evidence