HCID 118414938, compound → HCID 178469342, compound

Participants

Reaction Steps

A suspension of diethyl 2-(5-amino-3-methyl-1-(4-phenoxybenzyl)-1H-pyrazol-4-yl)-2-hydroxysuccinate (crude from above) (2.31 mmol) from x in glacial AcOH (14 mL) was refluxed for 2 h. The mixture was concentrated under reduced pressure as much as possible. Then MeOH was added and the product crystallized as a white solid which was filtered, washed with cold MeOH and dried in a vacuum oven to provide the title compound (628 mg, 67% over two steps) as a tan solid. 1H NMR (500 MHz, CDCl3) δ 7.40 (d, J=8.3 Hz, 2H), 7.31 (t, J=7.3 Hz, 2H), 7.09 (t, J=7.4 Hz, 1H), 6.97 (d, J=8.0 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 6.78 (s, 1H), 5.50 (s, 2H), 4.44 (q, J=7.1 Hz, 2H), 2.53 (s, 3H), 1.43 (t, J=7.1 Hz, 3H). 13C NMR (125 MHz, CDCl3) δ 164.83, 164.75, 157.17, 156.81, 143.45, 143.12, 139.06, 130.59, 129.72, 129.51, 123.43, 119.11, 118.70, 113.27, 103.16, 62.13, 50.60, 15.44, 14.16. ESI MS: m/z 404.1 (M+H)+.

Provenance & Evidence