Triethylamine → HCID 58387892, compound

HRID 2080267Notes

Reaction equation

HRID 2080267 reaction equation
S(Cl)(Cl)=O.[N:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]([OH:17])=O)=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>CN(C1C=CC=CN=1)C.O.C(OCC)(=O)C>[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([NH:29][C:15]([C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[N:5]=[CH:6][CH:7]=[CH:8]3)=[O:17])[CH:30]=[CH:31][CH:32]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 825716-Quinolinecarboxylic acidHCID 928923-Benzyloxyaniline

Product 1

HCID 58387892HCID 58387892, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Thionyl chloride (2 mL) was added to 6-quinolinecarboxylic acid (100 mg, 0.577 mmol), and the solution was stirred for 2 hours under reflux. Then, the solution was allowed to cool to room temperature, and excess thionyl chloride was evaporated in vacuo. The obtained residue was dissolved in N,N-dimethylformamide (2 mL), 3-benzyloxyaniline (115 mg, 0.577 mmol), triethylamine (0.12 mL, 0.866 mmol) and dimethylaminopyridine (1 mg) were added, and the solution was stirred overnight at room temperature. Ethyl acetate and water were added to the reaction solution, which was then partitioned, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (53 mg, 26%) was obtained as a white solid.

Workup

  1. temperatureunder reflux
  2. customexcess thionyl chloride was evaporated in vacuo
  3. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (2 mL)
  4. stirringthe solution was stirred overnight at room temperature
  5. customwas then partitioned
  6. washthe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-73415e2a586442f4acab1286b499e651
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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