Acetate → HCID 67491158, compound

HRID 1910719Notes

Reaction equation

HRID 1910719 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([NH2:14])[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2].[Cl:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C([O-])(=O)C.N1C=CC=CC=1>CN(C=O)C>[C:1]([N:4]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[C@H:7]([NH:14][C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=2)[CH2:6][C@@H:5]1[CH3:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 175AcetateHCID 1049PyridineHCID 742994-Chlorophenylboronic acidHCID 66700111HCID 66700111, compound

Product 1

HCID 67491158HCID 67491158, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[Step 4] 15 mg of the 1-acetyl-4-amino-2-methyl-3,4-dihydro-2H-[1,5] naphthyridine and 23 mg of 4-chlorophenylboronic acid were dissolved in 0.3 mL of DMF followed by adding 27 mg of divalent capper acetate and 18 μL of pyridine and stirring for 5 hours at room temperature in the presence of air. Following completion of the reaction, the solution was filtered with celite followed by the addition of water and 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 13 mg of the target compound in the form of a pale yellow solid (57%).

Workup

  1. customcompletion of the reaction
  2. filtrationthe solution was filtered with celite
  3. additionfollowed by the addition of water
  4. extractionextracting 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-d30f8d2313514662b79bbcbf2b96169a
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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