Benzyl Bromide → 3-Acetyl-4-(benzylamino)-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

HRID 13808

反応式

HRID 13808 の反応式
[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[NH2:14])=[CH:11][C:10]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[H-].[Na+]>C1COCC1>[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[NH:14][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[CH:11][C:10]([C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29])[N:8]=2)(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 7498Benzyl Bromide2 回HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 112600073-acetyl-4-amino-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

生成物 1

HCID 112499703-Acetyl-4-(benzylamino)-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-1,8-naphthyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of the product from Example 2 (50 mg), potassium carbonate (14 mg) and benzyl bromide (12 μL) in THF (2 mL) was stirred overnight. No progress of the reaction was observed. The reaction mixture was cooled to 0° C., followed by addition of sodium hydride (60% in mineral oil) (4 mg). The reaction was stirred for 10 min and benzyl bromide (12 μL) was added. The suspension was allowed to come to room temperature and stirred overnight. The reaction was quenched with water and extracted twice with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification on a preparative silica TLC plate eluted with 45% ethyl acetate in hexane afforded the title compound. HPLC/MS: 561.9 (M+1), 563.9 (M+3); Rt=5.09 min.

後処理

  1. customto come to room temperature
  2. stirringstirred overnight
  3. customThe reaction was quenched with water
  4. extractionextracted twice with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification on a preparative silica TLC plate
  10. washeluted with 45% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-dcd8940b025142f4b718327ad4333355
出典データセット
uspto-grants-2010_06
特許番号
US07728141B2

関連ノート

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