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 394183ノート

反応式

HRID 394183 の反応式
[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

参加物

4

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7455c8041f97409eb6b326d97a931f03
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

反応ノート

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