Ethyl Acetate → HCID 117667498, compound

HRID 712610Notes

Reaction equation

HRID 712610 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[N:16][CH:17]=2)[NH:14][CH2:13][CH2:12][CH2:11]3)[CH:5]=[N:6][CH:7]=1.[C:18]([N:26]=C=O)(=[O:25])C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]3[C:15](=[N:16][CH:17]=2)[N:14]([C:18]([NH2:26])=[O:25])[CH2:13][CH2:12][CH2:11]3)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 117667370HCID 117667370, compound

Product 1

HCID 117667498HCID 117667498, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

6-(5-Bromo-pyridin-3-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine (190 mg, 0.67 mmol) and benzoyl isocyanate (220 mg, 1.3 mmol) are mixed in 3.0 mL of DCM and the mixture is stirred at 50° C. for 2 hrs and room temperature for 16 hrs. Then the solvent is removed and the residue is suspended in 3.0 mL of EtOH. K2CO3 (160 mg, 1.1 mmol) is added and the mixture is heated at 70° C. for 30 min. Then the solvent is removed and the residue is partitioned between water (20 mL) and EtOAc (50 mL). The aqueous layer is separated and extracted with DCM (2×50 mL). The organic layers are combined and concentrated to give the crude product. To the crude product is added EtOAc (10 mL) and the solid formed is filtered, washed again with EtOAc (2×10 mL) and dried to give 158 mg of 6-(5-bromo-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid amide.

Workup

  1. customThen the solvent is removed
  2. temperaturethe mixture is heated at 70° C. for 30 min
  3. customThen the solvent is removed
  4. customthe residue is partitioned between water (20 mL) and EtOAc (50 mL)
  5. customThe aqueous layer is separated
  6. extractionextracted with DCM (2×50 mL)
  7. concentrationconcentrated
  8. customto give the crude product
  9. customthe solid formed
  10. filtrationis filtered
  11. washwashed again with EtOAc (2×10 mL)
  12. customdried

Sources & evidence

ORD record
ord-6691c43c5cb244aa90ef0dc3305b9773
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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