Methanesulfonamide → N-(azetidin-1-ylsulfonyl)-4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzamide

Participants

Reaction Steps

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace methanesulfonamide with azetidine-1-sulfonamide and to replace 4-(((1r,3r,5r,7r)-2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 4-(bicyclo[4.1.0]heptan-1-ylmethoxy)-5-cyclopropyl-2-fluorobenzoic acid, the title compound was obtained following purification by reverse-phase HPLC as a colorless powder (0.037 g, 37%): 1H NMR (300 MHz, DMSO-d6) δ 11.60 (br, s, 1H), 7.15 (d, J=8.3 Hz, 1H), 6.87 (d, J=13.0 Hz, 1H), 4.09-3.98 (m, 4H), 3.92-3.84 (m, 1H), 3.80-3.74 (m, 1H), 2.23-1.98 (m, 3H), 1.96-1.68 (m, 3H), 1.66-1.52 (m, 1H), 1.34-1.13 (m, 4H), 1.04-0.83 (m, 3H), 0.75-0.60 (m, 3H), 0.41-0.33 (m, 1H); MS (ES+) m/z 423.1 (M+1)

Provenance & Evidence