Potassium Carbonate → 2-Amino-5-(7-methoxybenzofuran-2-yl)pyrrole-3-carboxamide

HRID 416024Notes

Reaction equation

HRID 416024 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=2[CH:8]=1)(=O)[CH3:2].BrCC(C1OC2C(OC)=CC=CC=2C=1)=O.[CH2:30]([C:34]([NH2:36])=[O:35])[C:31]([NH2:33])=[NH:32].Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CN(C)C=O.O>[NH2:33][C:31]1[NH:32][C:1]([C:4]2[O:5][C:6]3[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:7]=3[CH:8]=2)=[CH:2][C:30]=1[C:34]([NH2:36])=[O:35]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 39378Ethanone, 1-(7-methoxy-2-benzofuranyl)-HCID 3084595Amidinomalonamide hydrochlorideHCID 826339572-Bromo-1-(7-methoxy-1-benzofuran-2-yl)ethan-1-one

Product 1

HCID 582940482-Amino-5-(7-methoxybenzofuran-2-yl)pyrrole-3-carboxamideYield 23%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phenylrimethylammonium tribromide (2.0 g, 5.3 mmol) was added to a solution of 2-acetyl-7-methoxybenzofuran (1.0 g, 5.3 mmol) in anhydrous tetrahydrofuran (25 mL), and the mixture was stirred at room temperature for 4 hours. After the insoluble solid was filtered out, the filtrate was concentrated in vacuo to give a mixture including 2-bromoacetyl-7-methoxybenzofuran. Malonamamidine hydrochloride (1.5 g, 11 mmol) and potassium carbonate (1.5 g, 11 mmol) were added to a solution of this mixture in anhydrous N,N-dimethylformamide (40 mL) and the whole was stirred at 60° C. overnight. After cooling, the reaction mixture was diluted with water (200 mL), and the whole was extracted with ethyl acetate (100 mL, twice). The organic layer was washed with brine (100 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, and the obtained residue was purified by silica gel column chromatography to give the title reference compound (0.33 g) as a dark green solid (Yield 23%).

Workup

  1. filtrationAfter the insoluble solid was filtered out
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a mixture
  4. stirringthe whole was stirred at 60° C. overnight
  5. temperatureAfter cooling
  6. extractionthe whole was extracted with ethyl acetate (100 mL
  7. washThe organic layer was washed with brine (100 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed in vacuo
  10. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b322b46377294260b93a1770185f13a0
Source dataset
uspto-grants-2012_01
Patent number
US08088817B2

Reaction notes

Loading…