Methanol → HCID 44464040, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-{3-cyclopentyl-2-[4-(2-cyclopentyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionylamino}-nicotinic acid methyl ester (Example 66, 130 mg, 0.24 mmol) in tetrahydrofuran (5.0 mL) at 25° C. was treated with a 0.5N aqueous lithium hydroxide solution (1.0 mL) and methanol (1.0 mL). The resulting solution was stirred at 25° C. for 5 h. After this time, the solution was concentrated in vacuo. The residue was treated with a 1N aqueous hydrochloric acid solution (0.6 mL). The mixture was extracted with ethyl acetate. The organics were then washed with a saturated aqueous sodium chloride solution and then concentrated in vacuo. The resulting solids were triturated with hexanes and diethyl ether. The resulting solids were collected by filtration and dried in vacuo to afford 6-{3-cyclopentyl-2-[4-(2-cyclopentyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionylamino}-nicotinic acid (38 mg) as a solid; ES+-HRMS m/e calcd for C29H32N4O5 [M+H+] 517.2446 found 517.2443. 1H-NMR (300 MHz, DMSO-d6) δ ppm 1.03-2.05 (m, 18H), 2.31 (m, 1H), 3.04 (m, 1H), 5.57 (dd, J=4.2, J=10.6 Hz, 1H), 5.61 (d, J=2.7 Hz, 1H), 7.20 (m, 1H), 7.27-7.38 (m, 2H), 7.49 (m, 1H), 8.08 (d, Jo=8.8 Hz, 1H), 8.20 (d, J=2.7 Hz, 1H), 8.24 (dd, Jo=8.8 Hz, Jm=2.2 Hz, 1H), 8.84 (d, Jm=2.2 Hz, 1H), 11.33 (s, 1H), 13.18 (br.s., 1H).

Provenance & Evidence