N,N-dimethyl-m-phenylenediamine → 6-((2-(3-(dimethylamino)phenylamino)pyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamide

HRID 16238

反応式

HRID 16238 の反応式
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:23])[C:9]2[CH:22]=[CH:21][C:12]3[C:13]([C:17]([NH:19][CH3:20])=[O:18])=[C:14]([CH3:16])[O:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:24][N:25]([CH3:33])[C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29]>CN(C=O)C>[CH3:24][N:25]([CH3:33])[C:26]1[CH:27]=[C:28]([NH:29][C:2]2[N:7]=[C:6]([N:8]([CH3:23])[C:9]3[CH:22]=[CH:21][C:12]4[C:13]([C:17]([NH:19][CH3:20])=[O:18])=[C:14]([CH3:16])[O:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH:30]=[CH:31][CH:32]=1

参加物

4

反応物 2

HCID 76084N,N-dimethyl-m-phenylenediamineHCID 592247476-((2-chloropyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamide

生成物 1

HCID 446344836-((2-(3-(dimethylamino)phenylamino)pyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamide収率 78%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

6-((2-chloropyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamide (0.1 mmol) and 3-dimethylaminoaniline (0.1 mmol) were dissolved in 0.5 ml DMF. To this was added p-TsOH monohydrate (0.2 mmol). The reaction mixture was stirred at 60° C. for 5 hours, and subjected to extraction with EtOAc. Then water was added and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated. The resulting residue was purified by column chromatography to provide the title product in a yield of 78%.

後処理

  1. extractionsubjected to extraction with EtOAc
  2. additionThen water was added
  3. extractionthe mixture was subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with water and brine sequentially
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography

出典と根拠

ORDレコード
ord-6319f4d90ee340cbb34c2715c3d9de01
出典データセット
uspto-grants-2010_06
特許番号
US07737157B2

関連ノート

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