(S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazol-3-amine → 3-cyclopentyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-N-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-propionamide

Participants

Reaction Steps

Using the method described in Example 17, 3-cyclopentyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (Intermediate 47) and 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-ylamine (Intermediate 5) afforded 3-cyclopentyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-N-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrazol-3-yl]-propionamide as a white solid as a mixture of diastereomers (142.6 mg, 38%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.17 (m, 2H), 1.25 (s, 3H), 1.30 (s, 3H), 1.35-1.77 (m, 7H), 1.86-2.02 (m, 1H), 2.20-2.33 (m, 1H), 3.73 (dd, J=8.3, 5.9 Hz, 1H), 3.97-4.17 (m, 3H), 4.30-4.41 (m, 1H), 5.46 (dd, J=10.6, 4.2 Hz, 1H), 6.03 (d, J=2.6 Hz, 1H), 6.39 (d, J=2.1 Hz, 1H), 7.31-7.55 (m, 3H), 7.59 (br s, 1H), 8.22-8.33 (m, 1H), 10.73-10.94 (m, 1H).

Provenance & Evidence