3-Methoxyaniline → 6-(2-(3-methoxyphenylamino)pyrimidin-4-yloxy)-N,2-dimethylbenzofuran-3-carboxamide

HRID 16240

Reaction equation

Cl[C:2]1[N:7]=[C:6]([O:8][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.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)[NH2:28]>CN(C=O)C>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([NH:28][C:2]2[N:7]=[C:6]([O:8][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:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

6-(2-chloropyrimidin-4-yloxy)-N,2-dimethylbenzofuran-3-carboxamide (0.1 mmol) and 3-methoxyaniline (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 ethyl acetate. 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 80%.

Workup

extractionsubjected to extraction with ethyl acetate
additionThen water was added
extractionthe mixture was subjected to extraction with ethyl acetate
washThe organic layer was washed with water and brine sequentially
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record: ord-6c9f9b57843d4fe9a20c843dfd7e6fce
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737157B2

Linked notes

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