1,1'-Carbonyldiimidazole → 3-Chloro-9-cyclohexylimidazo[1,5-a]pyrido[3,2-e]pyrazin-6(5h)-one

HRID 2068961Notes

Reaction equation

HRID 2068961 reaction equation
[NH2:1][C:2]1[C:3]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21]>>[Cl:8][C:6]1[CH:5]=[N:4][C:3]2[N:9]3[C:10]([CH:14]4[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]4)=[N:11][CH:12]=[C:13]3[C:20](=[O:21])[NH:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59198835HCID 59198835, compound

Product 1

HCID 591985613-Chloro-9-cyclohexylimidazo[1,5-a]pyrido[3,2-e]pyrazin-6(5h)-one

Procedure

3-Amino-5-chloro-2-(2-cyclohexyl-1H-imidazol-1-yl)pyridine as synthesized in Production Example 103, 838 mg, 1,1′-carbonyldiimidazole 983 mg and 1,2-chlorobenzene 25 mL were mixed and heated under reflux for 15 hours. Cooling the reaction liquid off, the precipitate was recovered by filtration and washed with methanol. The resulting crystals were dissolved in a liquid mixture of 2N hydrochloric acid and methanol, and the insoluble matter was separated by filtration. The filtrate was made weakly alkaline with saturated aqueous sodium hydrogencarbonate solution, and the precipitate was recovered by filtration. Drying the same in flowing air under heating, 620 mg of the title compound was obtained.

Workup

  1. additionwere mixed
  2. temperatureheated
  3. temperatureunder reflux for 15 hours
  4. temperatureCooling
  5. customthe reaction liquid off, the precipitate
  6. filtrationwas recovered by filtration
  7. washwashed with methanol
  8. dissolutionThe resulting crystals were dissolved in a liquid mixture of 2N hydrochloric acid and methanol
  9. customthe insoluble matter was separated by filtration
  10. filtrationthe precipitate was recovered by filtration
  11. customDrying the same
  12. temperatureunder heating

Sources & evidence

ORD record
ord-92838a55ef904607b861af0c872a646d
Source dataset
uspto-grants-2012_10
Patent number
US08299080B2

Reaction notes

Loading…