methyl 3-amino-1-methyl-1H-pyrazole-5-carboxylate → 5-{3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionylamino}-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

Participants

Reaction Steps

Using the method described in Example 11, 3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid (Intermediate 21) and 5-amino-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (Intermediate 8) afforded 5-{3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethyl-phenoxy)-6H-pyridazin-1-yl]-propionylamino}-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester as a white solid (22.1 mg, 17%); ES+-HRMS m/e calcd for C25H26N5O5F3 [M+H+] 534.1959 found 534.1959. 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.09 (m, 1H), 1.23-1.75 (m, 8H), 1.95 (m, 1H), 2.23 (m, 1H), 3.82 (s, 3H), 4.01 (s, 3H), 5.46 (dd, J=4.5, J=10.4 Hz, 1H), 5.93 (d, J=2.9 Hz, 1H), 6.95 (s, 1H), 7.53-7.60 (m, 2H), 7.83 (t, J=7.8 Hz, 1H), 7.90 (d, J=7.8 Hz, 1H), 8.19 (d, J=2.9 Hz, 1H), 11.06 (s, 1H).

Provenance & Evidence