Potassium Carbonate → HCID 86272002, compound

HRID 712596Notes

Reaction equation

HRID 712596 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[C:15](=[N:16][CH:17]=1)[NH:14][CH2:13][CH2:12][CH2:11]2.[C:18]([N:26]=C=O)(=[O:25])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[C:15](=[N:16][CH:17]=1)[N:14]([C:18]([NH2:26])=[O:25])[CH2:13][CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 117666806HCID 117666806, compound

Product 1

HCID 86272002HCID 86272002, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 6-(4-Methyl-pyridin-3-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine (50 mg, 0.22 mmol) in 5.0 mL of anhydrous DCM is added benzoyl isocyanate (39 mg, 0.24 mmol) and the solution is heated to reflux for 3 hrs. Then the solvent is removed in vacuo and to the residue is added 5.0 mL of EtOH. Then K2CO3 (61 mg, 44 mmol) is added and the mixture is heated to reflux for 5 hrs. After cooling down to room temperature, the solid is filtered off. The filtrate is evaporated to dryness. The residue is dissolved in DCM, washed with water and brine. The organic layer is separated, dried over Na2SO4, filtered and concentrated. The crude product is purified by preparative HPLC to give 14 mg of the titled product.

Workup

  1. temperaturethe solution is heated
  2. temperatureto reflux for 3 hrs
  3. customThen the solvent is removed in vacuo and to the residue
  4. additionis added 5.0 mL of EtOH
  5. temperaturethe mixture is heated
  6. temperatureto reflux for 5 hrs
  7. filtrationthe solid is filtered off
  8. customThe filtrate is evaporated to dryness
  9. dissolutionThe residue is dissolved in DCM
  10. washwashed with water and brine
  11. customThe organic layer is separated
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-abfa50694b9045089e3b226d56ed753d
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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