Sodium hydride → HCID 66913724, compound

HRID 2104614Notes

Reaction equation

HRID 2104614 reaction equation
[C:1](=[N:4][OH:5])([NH2:3])[CH3:2].[H-].[Na+].[C:8]1([C:14]2[C:23]3[C:18](=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][C:15]=2[C:28](OCC)=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH3:2][C:1]1[N:3]=[C:28]([C:15]2[CH:16]=[N:17][C:18]3[C:23]([C:14]=2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:25])[F:26])[O:5][N:4]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 66913232HCID 66913232, compound

Product 1

HCID 66913724HCID 66913724, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of acetamidoxime (148 mg, 2.0 mmol) and powdered 4A molecular sieves (0.5 g) in THF (5 mL) is treated with 60% NaH in oil (80 mg, 2.0 mmol) for 15 min at ambient temperature. The reaction is treated with ethyl 4-phenyl-8-(trifluoromethyl)quinoline-3-carboxylate (173 mg, 0.50 mmol) and heated at reflux for 22 h. The reaction is cooled, concentrated, treated with water, and extracted with dichloromethane. The extracts are dried with MgSO4, concentrated, and the residue chromatographed with 20:80 ethyl acetate:hexane to afford the title compound as an off-white solid (151 mg). MS (ES) m/z 356.1; HRMS: calcd for C19H12F3N3O, 355.0932; found (ESI, [M+H]+), 356.1008.

Workup

  1. temperatureheated
  2. temperatureat reflux for 22 h
  3. temperatureThe reaction is cooled
  4. concentrationconcentrated
  5. additiontreated with water
  6. extractionextracted with dichloromethane
  7. dry with materialThe extracts are dried with MgSO4
  8. concentrationconcentrated
  9. customthe residue chromatographed with 20:80 ethyl acetate

Sources & evidence

ORD record
ord-4edbea12bb6744778de4dccd3a61fcde
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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