Dimethylformamide → HCID 58168240, compound

HRID 1029097Notes

Reaction equation

HRID 1029097 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.CO[C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:32][N:33](C=O)C>>[O:14]=[C:6]1[C:5]2[CH:15]=[CH:16][C:2]([O:25][C:21]3[CH:22]=[CH:23][C:24]([C:32]#[N:33])=[CH:19][CH:20]=3)=[CH:3][C:4]=2[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 58168117HCID 58168117, compound

Product 1

HCID 58168240HCID 58168240, compoundYield 37%

Conditions

Temperature
180 °C

Procedure

9-Fluoro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.19 mmol), 3-methoxyphenol (70 mg, 0.56 mmol), and potassium carbonate (129 mg, 0.93 mmol) were suspended in DMF (1.5 mL), and stirred for 20 minutes at 180° C. in the microwave. The reaction mixture was quenched with H2O. The resulting precipitate was filtered and washed with H2O. The precipitate was triturated with MeOH, filtered, washed with MeOH, and dried under vacuum to provide 76 (22 mg, 37% yield) as a brown solid. LC-MS (M+H=319, obsd.=319). 1H NMR (400 MHz, d6-DMSO): δ 11.99 (s, 1H), 8.73 (dd, 1H), 8.50 (dd, 1H), 8.32 (d, 1H), 8.14 (d, 1H), 7.38 (t, 1H), 7.30 (dd, 1H), 7.22 (dd, 1H), 6.83 (dd, 1H), 6.77 (t, 1H), 6.71 (dd, 1H), 3.77 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O
  4. customThe precipitate was triturated with MeOH
  5. filtrationfiltered
  6. washwashed with MeOH
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0804b5166b674ec98adb86c3ee2898bb
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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