Dichloromethane → HCID 58460155, compound

HRID 1946484Notes

Reaction equation

HRID 1946484 reaction equation
Cl.[CH3:2][CH:3]([CH3:7])[C:4](=[NH:6])[NH2:5].Br[C:9]1[C:10](=O)[CH2:11][CH2:12][C:13]=1[O:14]C.C(=O)([O-])[O-].[K+].[K+].ClCCl>CN(C)C=O>[CH3:2][CH:3]([C:4]1[NH:5][C:10]2[CH2:11][CH2:12][C:13](=[O:14])[C:9]=2[N:6]=1)[CH3:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27820532-Methylpropanimidamide hydrochlorideHCID 110954262-Bromo-3-methoxycyclopent-2-enone

Product 1

HCID 58460155HCID 58460155, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-methylpropanimidamide hydrochloride (0.770 g), 2-bromo-3-(methyloxy)-2-cyclopenten-1-one (1 g) and potassium carbonate (2.17 g) in N,N-dimethylformamide (15 mL) were heated at 100° C. for 4.5 hr and then heated at 110° C. for 1 hour. The reaction mixture was cooled down to room temperature and dichloromethane was added. The white suspension (potassium carbonate) was filtered off and the filtrate concentrated under vacuum. The residue was purified by reverse phase chromatography using an acetonitrile—0.1% NH3:water—with an ammonium carbonate buffer modifier using a 5%-95% gradient. The desired fractions were combined and concentrated under vacuum to yield the title compound (531 mg). LC/MS MH+ 165, Rt 0.36 min (2 minute run).

Workup

  1. temperatureheated at 110° C. for 1 hour
  2. temperatureThe reaction mixture was cooled down to room temperature
  3. filtrationThe white suspension (potassium carbonate) was filtered off
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe residue was purified by reverse phase chromatography
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a7c1179e11c4404693992c6538ba499e
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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