Triethylamine → HCID 87114679, compound

HRID 1910728Notes

Reaction equation

HRID 1910728 reaction equation
C([C:8]1[C:13]2=[C:14]3[C:19](=[CH:20][CH:21]=[C:12]2[O:11][C:10](=[O:27])[CH:9]=1)[N:18]([C:22](=[O:24])[CH3:23])[C@@H:17]([CH3:25])[CH2:16][C@H:15]3[NH2:26])C1C=CC=CC=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:22]([N:18]1[C:19]2[C:14](=[C:13]3[CH:8]=[CH:9][C:10](=[O:27])[O:11][C:12]3=[CH:21][CH:20]=2)[C@H:15]([NH:26][C:32]2[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=2)[CH2:16][C@@H:17]1[CH3:25])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 742994-Chlorophenylboronic acidHCID 86664534HCID 86664534, compound

Product 1

HCID 87114679HCID 87114679, compoundYield 30.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

[Step 5] 22 mg of the cis-benzyl-7-acetyl-10-amino-8-methyl-7,8,9,10-tetrahydro-3H-pyrano[3,2-f]-quinolin-3-one and 19 mg of 4-chlorophenylboronic acid were dissolved in 10 mL of dichloromethane followed by adding 29 mg of divalent copper acetate and 34 μL of triethylamine and stirring for 18 hours at room temperature in the presence of air. Following completion of the reaction, the solution was filtered with celite and water was added followed by extracting three times with ethyl acetate. After washing with saturated brine and dehydrating with anhydrous sodium sulfate, the solution was concentrated under reduced pressure and the resulting residue was purified using silica gel chromatography (ethyl acetate:hexane=1:1) to obtain 7 mg of the target compound in the form of a yellow solid (23%).

Workup

  1. customcompletion of the reaction
  2. filtrationthe solution was filtered with celite and water
  3. additionwas added
  4. extractionby extracting three times with ethyl acetate
  5. washAfter washing with saturated brine
  6. concentrationthe solution was concentrated under reduced pressure
  7. customthe resulting residue was purified

Sources & evidence

ORD record
ord-f29a5ff6903f44d18873b8dcea2e6f0f
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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