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

HRID 16238
Notes
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Reaction equation

HRID 16238 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-6319f4d90ee340cbb34c2715c3d9de01
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07737157B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes