Ethyl Acetate → HCID 86305569, compound

HRID 712594Notes

Reaction equation

HRID 712594 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[NH:13][CH2:12][CH2:11][CH2:10]3)[CH:2]=1.[C:17]([N:25]=C=O)(=[O:24])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:14](=[N:15][CH:16]=2)[N:13]([C:17]([NH2:25])=[O:24])[CH2:12][CH2:11][CH2:10]3)[CH:2]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 117667315HCID 117667315, compound

Product 1

HCID 86305569HCID 86305569, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

6-Pyridin-3-yl-1,2,3,4-tetrahydro-[1,8]naphthyridine (50 mg, 0.24 mmol) and benzoyl isocyanate (58 mg, 0.36 mmol) are dissolved in 1.5 mL of DCM. The mixture is heated at 50° C. for 5 hrs. Then the solvent is removed in vacuum and the residue is dissolved in 1.5 mL of EtOH. K2CO3 (56 mg, 0.40 mmol) is added and the mixture is heated at 80° C. for 55 min. Then the solvent is removed and the residue is partitioned between water (35 mL) and EtOAc (55 mL). The aqueous layer is separated and extracted with EtOAc (2×30 mL). The organic layers are combined and concentrated to give the crude product. To the crude product is added EtOAc (1 mL) and the white solid formed is filtered, rinsed with EtOAc/heptane (1:1) mixture and dried to give 34 mg of the titled product.

Workup

  1. customThen the solvent is removed in vacuum
  2. dissolutionthe residue is dissolved in 1.5 mL of EtOH
  3. temperaturethe mixture is heated at 80° C. for 55 min
  4. customThen the solvent is removed
  5. customthe residue is partitioned between water (35 mL) and EtOAc (55 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with EtOAc (2×30 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customthe white solid formed
  11. filtrationis filtered
  12. washrinsed with EtOAc/heptane (1:1) mixture
  13. customdried

Sources & evidence

ORD record
ord-a58ee3fa1a32472c890214debc3dd9a5
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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