Example 19
The procedure described in Example 1 was followed, using a DMF (2 ml) solution of 2-[4-(trifluoromethyl)phenyl]cyclopropanecarboxylic acid (racemic) (100 mg, 0.434 mmol) [Journal of Organic Chemistry (1997), 62(26), 9114-9122.], EDC (125 mg, 0.651 mmol), HOBt (74 mg, 0.477 mmol), triethylamine (0.18 ml) and the compound of Example 2D (115 mg, 0.434 mmol). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and EtOAc (1/1) and isolated from MeOH to afford 20 mg (10% yield) of the title compound as white solids.
1H NMR (DMSOd-6, 300 MHz) δ ppm 1.32 (3H, d, J=7.3 Hz), 1.23-1.43 (2H, m), 1.99-2.05 (1H, m), 2.29 (3H, s), 2.28-2.39 (1H, m), 2.96 (3H, s), 4.85-4.96 (1H, m), 7.11-7.23 (3H, m), 7.36 (2H, d, J=8.1 Hz), 7.63 (2H, d, J=8.1 Hz), 8.56 (1H, d, J=8.1 Hz), 9.02 (1H, brs). MS (ESI): m/z 441 (M+H)+.
19b) N-((1R)-1-{3-Methyl-4-[(methylsulfonyl)amino]phenyl}ethyl)-2-[4-(trifluoromethyl)phenyl]cyclopropanecarboxamide (diastereomer Mixture)
Following Example 19a, the filtrate was evaporated under reduced pressure to give the title compound (80 mg, 42% yield) as the mixture of diastereomer products (1:2) as white solids.
1H NMR (300 MHz, DMSOd-6) δ 1.24-1.43 (5H, m), 1.99-2.05 (1H, m), 2.26-2.35 (4H, m), 2.94-2.96 (3H, m), 4.85-4.94 (1H, m), 7.09-7.23 (3H, m), 7.30-7.40 (2H, m), 7.57-7.64 (2H, m), 8.53-8.62 (1H, m), 8.99 (1H, brs). MS (ESI): m/z 441 (M+H)+.
