6-Hydroxy-3,4-dihydro-2(1H)-quinolinone → HCID 86623736, compound

Participants

Reaction Steps

Synthesized as described in Example 27B from 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (Example 15B) and 6-hydroxy-3,4-dihydro-2(1H)-quinolinone with the following exceptions: PPh3 was used instead of PBu3 and purification of the title compound consisted of flash chromatography (EtOAc/hexanes) followed by RP-HPLC (MeCN/H2O with 0.1% TFA): 1H NMR (400 MHz, acetone-D6) δ 8.96 (bs, 1H), 7.83 (d, J=8.9 Hz, 1H), 7.49 (d, J=2.7 Hz, 1H), 7.41 (dd, J=8.9, 2.7 Hz, 1H), 6.84 (d, J=8.6 Hz, 1H), 6.79 (d, J=2.6 Hz, 1H), 6.74 (dd, J=8.6 Hz, 1H), 4.62 (q, J=9.0 Hz, 2H), 4.31 (t, J=5.3 Hz, 2H), 4.16 (t, J=5.3-Hz, 2H), 2.88 (partially resolved dd, J≈7.5, 7.0 Hz, 2H), 2.44 (dd, J=8.6, 6.4 Hz, 2H).

Provenance & Evidence