Dichloromethane → HCID 58460205, compound

HRID 1946500Notes

Reaction equation

HRID 1946500 reaction equation
Cl.[CH3:2][C:3]([CH3:8])([CH3:7])[C:4](=[NH:6])[NH2:5].Br[C:10]1[C:11](=O)[CH2:12][CH2:13][C:14]=1[O:15]C.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CN(C)C=O>[CH3:2][C:3]([C:4]1[NH:5][C:11]2[CH2:12][CH2:13][C:14](=[O:15])[C:10]=2[N:6]=1)([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2781880Propanimidamide, 2,2-dimethyl-, hydrochloride (1:1)HCID 110954262-Bromo-3-methoxycyclopent-2-enone

Product 1

HCID 58460205HCID 58460205, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,2-dimethylpropanimidamide hydrochloride (0.858 g), 2-bromo-3-(methyloxy)-2-cyclopenten-1-one (1 g) and potassium carbonate (2.53 g) in N,N-dimethylformamide (15 mL) were heated at 80° C. for 20 h. The reaction mixture was cooled down to room temperature and DCM (20 mL) was added. The mixture was filtered and the filtrate concentrated under vacuum. The residue was purified by reverse phase chromatography using Acetonitrile Water with an ammonium carbonate modifier gradient (5-40%). The desired fractions were combined and concentrated under vacuum to yield 685 mg of the title compound. LC/MS MH+ 179, Rt 1.48 min (5 minute run).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe residue was purified by reverse phase chromatography
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dce57460e0104f98b749fefb74e2b994
Source dataset
uspto-grants-2013_03
Patent number
US08399444B2

Reaction notes

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