Ethyl Acetate → HCID 86305665, compound

HRID 712599Notes

Reaction equation

HRID 712599 reaction equation
[N:1]1[C:10]2[NH:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:11]2[CH:12]=[C:13]([C:17](=[O:19])[CH3:18])[CH:14]=[N:15][CH:16]=2)[CH:2]=1.[C:20]([N:28]=C=O)(=[O:27])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C(Cl)Cl>[C:17]([C:13]1[CH:12]=[C:11]([C:3]2[CH:4]=[C:5]3[C:10](=[N:1][CH:2]=2)[N:9]([C:20]([NH2:28])=[O:27])[CH2:8][CH2:7][CH2:6]3)[CH:16]=[N:15][CH:14]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 117667561HCID 117667561, compound

Product 1

HCID 86305665HCID 86305665, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

1-[5-(5,6,7,8-Tetrahydro-[1,8]naphthyridin-3-yl)-pyridin-3-yl]-ethanone (50 mg, 0.20 mmol) and benzoyl isocyanate (48 mg, 0.30 mmol) are dissolved in 2.0 mL of DCM. The mixture is heated at 50° C. for 16 hrs. Then the solvent is removed in vacuum and the residue is dissolved in 2.0 mL of EtOH. K2CO3 (46 mg, 0.34 mmol) is added and the mixture is heated at 80° C. for 45 min. The solvent is removed and the residue is partitioned between water (35 mL) and EtOAc (75 mL). The aqueous layer is separated and extracted with DCM (2×30 mL). The organic layers are combined and concentrated to give the crude product. EtOAc (2 mL) is added to the crude and the white solid formed is filtered, rinsed with more EtOAc (2×3 mL) and dried to give 30 mg of the titled product.

Workup

  1. customThen the solvent is removed in vacuum
  2. dissolutionthe residue is dissolved in 2.0 mL of EtOH
  3. temperaturethe mixture is heated at 80° C. for 45 min
  4. customThe solvent is removed
  5. customthe residue is partitioned between water (35 mL) and EtOAc (75 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with DCM (2×30 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customthe white solid formed
  11. filtrationis filtered
  12. washrinsed with more EtOAc (2×3 mL)
  13. customdried

Sources & evidence

ORD record
ord-99b4d90dee564c9596d979d12ec0467b
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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