Hydrochloric Acid → HCID 24994084, compound

HRID 2066920Notes

Reaction equation

HRID 2066920 reaction equation
[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[N:3][CH:2]=1)[C:14]1[C:13](=[O:18])[NH:12][CH2:11][CH2:10][C:9]=1[NH:8]3.[F:19][C:20]([F:31])([F:30])[CH2:21]OS(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Cl>CN(C=O)C.CO>[F:19][C:20]([F:31])([F:30])[CH2:21][N:8]1[C:7]2[C:15](=[CH:16][CH:17]=[C:5]3[CH:4]=[N:3][CH:2]=[CH:1][C:6]3=2)[C:14]2[C:13](=[O:18])[NH:12][CH2:11][CH2:10][C:9]1=2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium Carbonate2×HCID 2855718-Crown-62×HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate2×HCID 11402137HCID 11402137, compound

Product 1

HCID 24994084HCID 24994084, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 8,9,10,11-tetrahydro-3,8,11-triaza-benzo[a]fluoren-7-one (213 mg, 0.9 mmol), trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester (317 mg, 1.35 mmol), potassium carbonate (253 mg, 1.8 mmol) and 18-crown-6 ether (481 mg, 1.8 mmol) in anhydrous DMF (20 mL) was stirred under heating at 65° C. for 3 hours. More trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester (200 mg, 0.86 mmol), potassium carbonate (253 mg, 1.8 mmol) and 18-crown-6 (240 mg, 0.9 mmol) were added and heating continued for 3 hours. After cooling, the solvent was evaporated under vacuum and the crude product was purified by flash chromatography with DCM/MeOH 95:5 as eluant, affording a solid product. The solid product was then dissolved in methanol and treated with 1.25M HCl in methanol to pH 1. The solvent was removed under vacuum and the residue was treated with diethylether. The resulting solid was filtered, washed with diethylether, and dried under vacuum, affording 127 mg of the title compound as hydrochloric salt (39% yield).

Workup

  1. temperatureheating
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under vacuum
  4. customthe crude product was purified by flash chromatography with DCM/MeOH 95:5 as eluant
  5. customaffording a solid product
  6. customThe solvent was removed under vacuum
  7. additionthe residue was treated with diethylether
  8. filtrationThe resulting solid was filtered
  9. washwashed with diethylether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-6273921d93e84d8da64a58d3267b74c8
Source dataset
uspto-grants-2012_10
Patent number
US08293762B2

Reaction notes

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