Dimethylcarbamoyl Chloride → N'-[3-Acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]-N,N-dimethylurea

HRID 13809

反応式

HRID 13809 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].[H-].[Na+].[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>C1COCC1>[C:1]([C:4]1[C:5](=[O:31])[N:6]([CH3:30])[C:7]2[C:12]([C:13]=1[NH:14][C:36](=[O:37])[N:35]([CH3:39])[CH3:34])=[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

5

反応物 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 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 11489632N'-[3-Acetyl-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-1-methyl-2-oxo-1,2-dihydro-1,8-naphthyridin-4-yl]-N,N-dimethylurea

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of the product from Example 2 (70 mg) in THF (1 mL), under nitrogen, was cooled to 0° C. and treated with sodium hydride (60% in mineral oil) (7 mg). The suspension was stirred for 10 min were upon dimethylcarbamyl chloride (15 uL) was added. The reaction was allowed to warm to room temperature and was stirred overnight. The reaction mixture was quenched with water and extracted twice with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification on a preparative silica TLC plate eluted with 50% EtOAc in hexane afforded the title compound. HPLC/MS: 543.0 (M+1), 545.0 (M+3); Rt=4.27 min.

後処理

  1. additionwas added
  2. stirringwas stirred overnight
  3. customThe reaction mixture was quenched with water
  4. extractionextracted twice with ethyl acetate
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification on a preparative silica TLC plate
  9. washeluted with 50% EtOAc in hexane

出典と根拠

ORDレコード
ord-7b7099260b6c452e86cd05ada177bb67
出典データセット
uspto-grants-2010_06
特許番号
US07728141B2

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