Dimethylformamide → 1-(4-Cyano-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029114Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.N[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:31][N:32](C=O)C>CO>[C:31]([C:23]1[CH:22]=[CH:21][C:20]([O:24][C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)=[CH:19][CH:18]=1)#[N:32]

Participants

Conditions

Temperature: 100 °C

Procedure

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (30 mg, 0.13 mmol), 3-aminophenol (43 mg, 0.39 mmol), and potassium carbonate (90 mg, 0.65 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction mixture was diluted with MeOH, and filtered through a membrane. The crude product was purified via prep-LC-MS to provide 132 (3 mg, 8% yield) as a solid. LC-MS (M+H=304, obsd.=304). 1H NMR (400 MHz, d6-DMSO): δ 12.09 (s, 1H), 9.04 (d, 1H), 8.42 (dd, 1H), 8.28 (d, 1H), 7.78 (dt, 1H), 7.69 (t, 1H), 7.13 (t, 1H), 6.63 (d, 1H), 6.52 (dd, 1H), 6.39 (m, 2H), 5.54 (s, 2H).

Workup

filtrationfiltered through a membrane
customThe crude product was purified via prep-LC-MS

Sources & evidence

ORD record: ord-137190f555f7430a8b987424cf52d89f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735584B2

Reaction notes

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