2-Methoxyethylamine → HCID 22335356, compound

HRID 586713Notes

Reaction equation

HRID 586713 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13](Cl)[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21][CH2:22][NH2:23]>S([O-])([O-])(=O)=O.[Cu+2]>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13]([NH:23][CH2:22][CH2:21][O:20][CH3:19])[CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 162287476-Benzyl-2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 1

HCID 22335356HCID 22335356, compound

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Procedure

Copper (II) sulphate (200 mg) was added to a solution of 6-benzyl-2-chloro-5,6,7,8-tetrahydro-[1,6]naphthyridine (4.5 g, 17.4 mmol)(see reference WO9830560 Example 33 b) in 2-methoxyethylamine and the mixture was heated under reflux for 20 hours. The mixture was evaporated under reduced pressure and the residue was partitioned between dichloromethane (100 ml) and water (50 ml). The aqueous phase was extracted with dichloromethane (2×50 ml) and the combined organic phases were dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using methanol in dichloromethane as eluant (gradient from 1:99 to 3:97) to give the title compound as an orange oil (1.32 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. customThe mixture was evaporated under reduced pressure
  4. customthe residue was partitioned between dichloromethane (100 ml) and water (50 ml)
  5. extractionThe aqueous phase was extracted with dichloromethane (2×50 ml)
  6. dry with materialthe combined organic phases were dried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1cc2ad42002b44ce974a6abef9d1d76f
Source dataset
uspto-grants-2005_08
Patent number
US06936619B2

Reaction notes

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