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

HRID 16238

반응식

HRID 16238 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-6319f4d90ee340cbb34c2715c3d9de01
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737157B2

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