Di(succinimido) carbonate → 1-Allyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one

HRID 2112911Notes

Reaction equation

HRID 2112911 reaction equation
C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:3](=[O:4])C1.[CH2:19]([NH:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([Cl:29])[C:24]=1[NH2:30])[CH:20]=[CH2:21]>C(#N)C>[CH2:19]([N:22]1[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([Cl:29])[C:24]=2[NH:30][C:3]1=[O:4])[CH:20]=[CH2:21]

Participants

4

Reactant 2

HCID 676246Di(succinimido) carbonateHCID 57642851N*4*-Allyl-2-chloropyridin-3,4-diamine

Product 1

HCID 230708521-Allyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of N,N′-disuccinimidyl carbonate (4.46 g) in acetonitrile (400 mL) was added to a solution of N*4*-allyl-2-chloropyridine-3,4-diamine (2.88 g) in acetonitrile. This was then heated under reflux for 70 hours. The solvent was removed under reduced pressure, the residue was dissolved in ethyl acetate (500 mL) and water (300 mL). The organic layer was then washed twice with 100 mL of 1 N hydrochloric acid and then once with 100 mL of saturated aqueous sodium chloride solution. This was then dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the fraction eluted by ethyl acetate-dichloromethane (1:1) gave the title compound (2.30 g).

Workup

  1. temperatureThis was then heated
  2. temperatureunder reflux for 70 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate (500 mL)
  5. washThe organic layer was then washed twice with 100 mL of 1 N hydrochloric acid
  6. dry with materialThis was then dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography
  9. washthe fraction eluted by ethyl acetate-dichloromethane (1:1)

Sources & evidence

ORD record
ord-c4325ff40f7840cfa423aa7f022fe21b
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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