Phenyl isocyanate → HCID 22388288, compound

HRID 1072927Notes

Reaction equation

HRID 1072927 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[CH3:20])=[C:4]([Cl:23])[CH:3]=1.[C:24]1([N:30]=[C:31]=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[Cl:23][C:4]1[CH:3]=[C:2]([NH:1][C:31]([NH:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:32])[CH:22]=[CH:21][C:5]=1[CH2:6][N:7]1[C:11]2=[N:12][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:15]=[C:10]2[N:9]=[C:8]1[CH3:20]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 22388007HCID 22388007, compound

Product 1

HCID 22388288HCID 22388288, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 3-(4-amino-2-chlorobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (275 mg) was suspended in toluene (10 ml), and phenyl isocyanate (218 mg) was added at room temperature. The mixture was refluxed under heating for 5 hr and concentrated under reduced pressure. Hexane (20 ml) was added, and the mixture was heated and allowed to cool. The precipitated crystals were collected by filtration. The crystals were suspended in ethyl acetate (10 ml), heated and allowed to cool. The precipitated crystals were collected by filtration and dried under reduced pressure and by heating to give the objective compound (328 mg) as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 5 hr
  3. concentrationconcentrated under reduced pressure
  4. additionHexane (20 ml) was added
  5. temperaturethe mixture was heated
  6. temperatureto cool
  7. filtrationThe precipitated crystals were collected by filtration
  8. temperatureheated
  9. temperatureto cool
  10. filtrationThe precipitated crystals were collected by filtration
  11. customdried under reduced pressure
  12. temperatureby heating

Sources & evidence

ORD record
ord-f9b61705e4764267a73eef082f0fbeb6
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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