Ethyl Acetate → HCID 66769562, compound

Participants

Reaction Steps

A solution of 2-[(5-chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-5-fluorobenzonitrile (1.3 g, 3.38 mmol) in sodium hydroxide −1 M (10 mL, 10.00 mmol) and 1,4-dioxane (10 mL) was refluxed overnight. Ethyl acetate was added and the layers were separated. The organic layer was washed with 1 M NaOH (40 ml). The combined aqueous layers were washed with ethyl acetate, and neutralized with acetic acid. The product was isolated by filtration. 2-[(5-Chloro-2-{[3-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-5-fluorobenzoic acid (1.1 g, 2.72 mmol, 27.2% yield) was isolated as a yellow solid. 1H NMR (400 MHz, DMSO-d6) ppm 1.27 (d, J=6.57 Hz, 6 H) 2.11 (s, 3 H) 4.39 (quin, J=6.57 Hz, 1 H) 5.95 (s, 1 H) 6.70 (s, 1 H) 7.51 (td, J=8.40, 3.16 Hz, 1 H) 7.61 (dd, J=9.09, 4.80 Hz, 1 H) 7.72 (dd, J=9.22, 3.16 Hz, 1 H) 8.00 (s, 1 H) 8.53 (s, 1 H) 9.66 (br. s., 1 H) 13.88 (br. s., 1 H); HPLC Rt=2.44 min, MS (ESI): 404.3 [M+H]+.

Provenance & Evidence