Nitric Acid → HCID 59375493, compound

HRID 2192978Notes

Reaction equation

HRID 2192978 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:27]=[CH:26][C:9]2[C:10]([NH:19][CH:20]([CH3:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[N:11][C:12]3[CH:13]=[CH:14][NH:15][C:16](=[O:18])[C:17]=3[C:8]=2[CH:7]=1>C(O)(C(F)(F)F)=O.ClCCl>[Br:5][C:6]1[CH:27]=[CH:26][C:9]2[C:10]([NH:19][CH:20]([CH3:25])[C:21]([CH3:22])([CH3:23])[CH3:24])=[N:11][C:12]3[C:13]([N+:1]([O-:4])=[O:2])=[CH:14][NH:15][C:16](=[O:18])[C:17]=3[C:8]=2[CH:7]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 25097260HCID 25097260, compound

Product 1

HCID 59375493HCID 59375493, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

Nitric acid (0.271 mL, 4.24 mmol) was added to 9-bromo-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (397 mg, 1.061 mmol) in TFA (10.600 mL) at room temperature. Reaction was then heated to 40° C. and stirred for 1.5 h. The reaction was then diluted with dichloromethane (150 mL) and quenched by pouring cautiously into saturated NaHCO3. The layers were separated and the aqueous phase was further extracted with a 75 mL portion of dichloromethane. The combined organic layers were then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, loading with THF/hexanes and eluting with EtOAc/Hexanes to give the title compound as an orange solid. 1H NMR (500 MHz, C2D6SO) δ 12.11 (s, 1H), 9.98 (d, 1H, J=2.0 Hz), 8.55 (d, 11-1, J=9.0 Hz), 8.44 (s, 1H), 7.95 (d, 1H, J=9.0 Hz), 7.85 (dd, 1H, J=8.5, 2.0 Hz), 4.69 (m, 1H), 1.17 (d, 3H, J=7.0 Hz), 0.94 (s, 9H). LRMS (ESI) calc'd for (C18H20BrN4O3) [M+H]+ 419.1; found 419.0.

Workup

  1. customReaction
  2. customquenched
  3. additionby pouring cautiously into saturated NaHCO3
  4. customThe layers were separated
  5. extractionthe aqueous phase was further extracted with a 75 mL portion of dichloromethane
  6. dry with materialThe combined organic layers were then dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel, loading with THF/hexanes
  10. washeluting with EtOAc/Hexanes

Sources & evidence

ORD record
ord-3cfcc12b3df44ae1b396d84311197fe5
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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