Dimethylformamide → HCID 86724155, compound

Participants

Reaction Steps

To a mixture of 4-(3-carboxy-1-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)propyl)-3-methylbenzoic acid (1.08 g, 2.61 mmol) and K2CO3 (1.44 g, 10.44 mmol) in DMF (20 mL) was added iodomethane (0.82 mL, 13.05 mmol). The mixture was stirred at rt for about 4 h then partitioned between EtOAc (150 mL) and H2O (150 mL). The organic layer was washed with brine (2×200 mL), dried over Na2SO4, filtered and concentrated in vacuo to give methyl 4-(1-(5-chloro-1-methyl-3-(pyridin-2-yl)-1H-pyrazol-4-yl)-4-methoxy-4-oxobutyl)-3-methylbenzoate (1.03 g, 89%): LC-MS (Table 1, Method g) Rt=2.50 min, m/z 442 (M+H)+; 1H-NMR (DMSO, Bruker 400 MHz) δ 8.59-8.56 (m, 1H), 7.87-7.80 (m, 2H), 7.75-7.71 (m, 1H), 7.66 (d, J=1.4 Hz, 1H), 7.55 (d, J=8.2 Hz, 1H), 7.37-7.29 (m, 1H), 5.42-5.37 (m, 1H), 3.83 (s, 3H), 3.80 (s, 3H), 3.50 (s, 3H), 2.48-2.22 (m, 4H), 2.12 (s, 3H).

Provenance & Evidence