Triethylamine → HCID 68978375, compound

Participants

Reaction Steps

Ethyl thioglycolate (also referred to as mercapto-acetic acid ethyl ester) Compound 4f (0.57 g, 4.75 mmol) and triethylamine (0.78 mL, 5.54 mmol) were added to a solution of 4-chloro-6-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrimidine-5-carbonitrile Compound 4e (1.5 g, 3.96 mmol) in THF (20 mL) at RT under nitrogen. The reaction mixture was refluxed for 6 hours, then partitioned between ethyl acetate and water. The organic layer washed with aqueous 10% NH4Cl, water and brine, then dried (Na2SO4), filtered and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified via flash chromatography (1% methanol/dichloromethane) to yield {5-cyano-6-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrimidin-4-ylsulfanyl}-acetic acid ethyl ester Compound 4g (0.83 g, 45%) as a solid. 1H NMR (400 MHz, DMSO) δ 9.99 (1H, br s), 8.42 (1H, s), 8.13 (1H, d), 7.82 (1H, d), 7.82 (1H, d, J=8.9 Hz), 7.43 (1H, dd, J=1.9 Hz & 8.9 Hz), 7.36-7.34 (1H, m), 7.11-7.02 (3H, m), 5.69 (2H, s), 4.15-4.10 (4H, m), 1.18 (3H, t); MS (ES+) m/z 463.0 (MH+).

Provenance & Evidence