HCID 43446585, compound → N-(1-(2-(dimethylamino)ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide

HRID 1922342Notes

Reaction equation

HRID 1922342 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[C:7](=[O:17])[CH2:6][CH2:5]2.I.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](SC)=[NH:25]>C(O)C.CCOCC>[CH3:16][N:14]([CH3:15])[CH2:13][CH2:12][N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:24]([C:20]3[S:19][CH:23]=[CH:22][CH:21]=3)=[NH:25])=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:7]1=[O:17]

Participants

5

Reactant 2

HCID 43446585HCID 43446585, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178483722N-(1-(2-(dimethylamino)ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 6-amino-1-(2-(dimethylamino)ethyl)-3,4-dihydroquinolin-2(1H)-one (0.280 g, 1.20 mmol) in absolute ethanol (5 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.684 g, 2.40 mmol) at room temperature and the resulting mixture was stirred overnight (18 h). The reaction was diluted with ether (45 mL) and the precipitate collected by vacuum filtration. The precipitate was washed from the filter with methanol and the solvent was evaporated. The residue was diluted with 1N sodium hydroxide solution (5 mL) and product was extracted into ethyl acetate (3×10 ml). The combined ethyl acetate layer was washed with brine and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M ammonia in methanol:dichloromethane, 1:19). Product was dried under high vacuum. Yield: 230 mg of yellow oil 3 (56%).

Workup

  1. filtrationthe precipitate collected by vacuum filtration
  2. washThe precipitate was washed from the
  3. filtrationfilter with methanol
  4. customthe solvent was evaporated
  5. additionThe residue was diluted with 1N sodium hydroxide solution (5 mL) and product
  6. extractionwas extracted into ethyl acetate (3×10 ml)
  7. washThe combined ethyl acetate layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. customSolvent was evaporated
  10. customcrude was purified by column chromatography (2M ammonia in methanol:dichloromethane, 1:19)
  11. customProduct was dried under high vacuum

Sources & evidence

ORD record
ord-4f3ee861a570485b8cfa63c18a6e5e56
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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