Sodium Iodide → 2-{5-[2-(4-methoxy-phenyl)-ethyl]-7,8-dihydro-5H-[1,6]naphthyridin-6-yl}-N-methyl-2-phenyl-acetamide

HRID 563928Notes

Reaction equation

HRID 563928 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]2[NH:20][CH2:19][CH2:18][C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]2=3)=[CH:5][CH:4]=1.Br[CH:22]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:23]([NH:25][CH3:26])=[O:24].C(N(C(C)C)C(C)C)C.[I-].[Na+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]2[N:20]([CH:22]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:23]([NH:25][CH3:26])=[O:24])[CH2:19][CH2:18][C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]2=3)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 124711602-Bromo-N-methyl-2-phenylacetamideHCID 598199895-[2-(4-Methoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-[1,6]naphthyridine

Product 1

HCID 250275602-{5-[2-(4-methoxy-phenyl)-ethyl]-7,8-dihydro-5H-[1,6]naphthyridin-6-yl}-N-methyl-2-phenyl-acetamideYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 615 mg (2.29 mmol) 5-[2-(4-methoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-[1,6]naphthyridine in 25 mL acetonitrile, were added 682 mg (2.98 mmol) 2-bromo-N-methyl -2-phenyl-acetamide, 1.2 mL (6.87 mmol) N-ethyldiisopropylamine and 343 mg (2.29 mmol) sodium iodide. The solution was stirred at 60° C. for 6 h. The solvent was removed in vacuo and the residue was taken in ethyl acetate. The mixture was washed once with water and once with a 2M Na2CO3 solution, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on silica eluting with a gradient formed from heptane and ethyl acetate. The product containing fractions were evaporated to yield 330 mg (35%) of 2-{5-[2-(4-methoxy-phenyl)-ethyl]-7,8-dihydro-5H-[1,6]naphthyridin-6-yl}-N-methyl-2-phenyl-acetamide (diastereoisomer 1, first eluting diastereoisomer) as yellow foam

Workup

  1. customThe solvent was removed in vacuo
  2. washThe mixture was washed once with water and once with a 2M Na2CO3 solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica eluting with a gradient
  7. customformed from heptane and ethyl acetate
  8. additionThe product containing fractions
  9. customwere evaporated

Sources & evidence

ORD record
ord-f78206fe009d4255866f5f80c5b47e64
Source dataset
uspto-grants-2011_11
Patent number
US08067598B2

Reaction notes

Loading…