Pyrazole → HCID 59198637, compound

HRID 576826Notes

Reaction equation

HRID 576826 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[N:13][CH:14]=[C:7]1[C:6](=[O:21])[NH:5]2.[NH:22]1[CH:26]=[CH:25][CH:24]=[N:23]1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>[Cu](I)I.O>[CH:15]1([C:12]2[N:8]3[C:9]4[C:4]([NH:5][C:6](=[O:21])[C:7]3=[CH:14][N:13]=2)=[CH:3][C:2]([N:22]2[CH:26]=[CH:25][CH:24]=[N:23]2)=[CH:11][CH:10]=4)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 591987847-Bromo-1-cyclohexylimidazo[1,5-a]quinoxalin-4(5H)-one

Product 1

HCID 59198637HCID 59198637, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

7-Bromo-1-cyclohexylimidazo[1,5-a]quinoxalin-4(5H)-one as synthesized in above Example 145, 200 mg, pyrazole 59 mg, potassium carbonate 120 mg, copper iodide 28 mg and N,N-dimethylformamide 4 mL were mixed and stirred for 22 hours at 160° C. The reaction liquid was poured into water, and the precipitated matter was recovered by filtration. The precipitate was mixed with 25% aqueous ammonia and methanol, and heated under stirring. The insoluble matter was recovered by filtration, washed with water and dried by heating under reduced pressure to provide 30 mg of the title compound.

Workup

  1. additionwere mixed
  2. customThe reaction liquid
  3. filtrationthe precipitated matter was recovered by filtration
  4. additionThe precipitate was mixed with 25% aqueous ammonia and methanol
  5. temperatureheated
  6. stirringunder stirring
  7. filtrationThe insoluble matter was recovered by filtration
  8. washwashed with water
  9. customdried
  10. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-5076832cb6284b48a52dcb8002dfedb4
Source dataset
uspto-grants-2015_05
Patent number
US09040536B2

Reaction notes

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