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

HRID 1173432Notes

Reaction equation

HRID 1173432 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.O[C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])[CH2:27][CH2:26]2>>[O:33]=[C:28]1[CH2:27][CH2:26][C:25]2[C:30](=[CH:31][CH:32]=[C:23]([O:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:19])([F:20])[F:21])[C:5]3[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:15])([F:16])[F:14])[CH:6]=3)[CH:24]=2)[NH:29]1

Participants

3

Reactant 2

HCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinoneHCID 866237314-[(2-Hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 86623736HCID 86623736, compound

Procedure

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).

Workup

  1. customSynthesized
  2. customPPh3 was used instead of PBu3 and purification of the title compound

Sources & evidence

ORD record
ord-a073b4416a4841c5b3e1e0a670498c39
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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