Butanedione → HCID 178474136, compound

HRID 1990902Notes

Reaction equation

HRID 1990902 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1)(=[NH:4])[NH2:3].[CH3:15][C:16](=O)[C:17](=[O:19])C.[CH3:21]C(O)C>>[OH:19][CH2:17][C:16]1[NH:3][C:2]([C:5]2[CH:6]=[C:7]([NH:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][CH:10]=2)=[N:4][C:15]=1[CH3:21]

Participants

4

Reactant 3

HCID 650ButanedioneHCID 3776IsopropanolHCID 68699257HCID 68699257, compound

Product 1

HCID 178474136HCID 178474136, compoundYield 23%

Procedure

To a solution of N-(3-carbamimidoyl-phenyl)-acetamide hydrochloride (9.75 g, 45.6 mmol, 1.0 equiv; [CAS RN 521269-31-8], prepared according to WO 03/037 327 A1 (Hoffmann-La Roche A G)) in 2-propanol (180 mL) was added butane-2,3-dione (4.91 g, 57.0 mmol, 1.25 equiv). After heating to reflux for 20 h, the solvent was removed by evaporation under reduced pressure, water (20 mL) and 4 M HCl (40 mL) were added and the reaction mixture heated to reflux for an additional time period of 16 h. The reaction mixture was cooled down to rt, concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with dichloromethane/methanol (95:5) to give 2.6 g (23%) of the title compound. MS (ISP): 246.2 [M+H]+.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 20 h
  3. customthe solvent was removed by evaporation under reduced pressure, water (20 mL) and 4 M HCl (40 mL)
  4. additionwere added
  5. temperaturethe reaction mixture heated
  6. temperatureto reflux for an additional time period of 16 h
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customthe crude reaction product
  9. custompurified with column chromatography on silica eluting with dichloromethane/methanol (95:5)

Sources & evidence

ORD record
ord-9cdfb373c50c4fd38230778c3a9d320a
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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