7-(8-azabicyclo[3.2.1]oct-2-en-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one → 7-(8-azabicyclo[3.2.1]oct-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

HRID 394183Notes

Reaction equation

HRID 394183 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][C:3]([C:9]1[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][C:15](=[O:27])[N:16]3[C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])=[C:11]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[Cl:35])[N:10]=1)=[CH:2]2>C(OCC)(=O)C.O=[Pt]=O>[CH:5]12[NH:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][CH:3]([C:9]1[CH:18]=[C:17]3[C:12]([CH:13]=[CH:14][C:15](=[O:27])[N:16]3[C:19]3[C:20]([Cl:26])=[CH:21][CH:22]=[CH:23][C:24]=3[Cl:25])=[C:11]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[Cl:35])[N:10]=1)[CH2:4]2

Participants

4

Reactant 1

HCID 226479477-(8-azabicyclo[3.2.1]oct-2-en-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

Product 1

HCID 226481247-(8-azabicyclo[3.2.1]oct-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

39 mg of PtO2 (Adam's catalyst) was added to the mixture of 7-(8-azabicyclo[3.2.1]oct-2-en-3-yl)-5-(2chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (77 mg) in 2 mL ethyl acetate. The resulting reaction mixture was evacuated and purged with argon. Then hydrogen was bubbled through and the reaction mixture was stirred under hydrogen for 8 h. The reaction mixture was filtered, concentrated under reduced pressure, and purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-2M NH3 in methanol to yield 7-(8-azabicyclo[3.2.1]oct-3-yl)-5-(2-chloro-4-fluorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one. Mass spectrum (ESI) 528.6 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. customwas evacuated
  3. custompurged with argon
  4. customThen hydrogen was bubbled through and the reaction mixture
  5. filtrationThe reaction mixture was filtered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by preparative thin-layer chromatography
  8. washeluting with 95:5 CH2Cl2-2M NH3 in methanol

Sources & evidence

ORD record
ord-7455c8041f97409eb6b326d97a931f03
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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