Imidazole → HCID 22614895, compound

HRID 842681Notes

Reaction equation

HRID 842681 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Cl:6][C:7]1[C:8]([N:22]2[C:26]([CH3:27])=[N:25][N:24]=[C:23]2Br)=[C:9]2[C:14](=[CH:15][C:16]=1[Cl:17])[N:13]=[C:12]([O:18][CH3:19])[C:11]([O:20][CH3:21])=[N:10]2>>[Cl:6][C:7]1[C:8]([N:22]2[C:26]([CH3:27])=[N:25][N:24]=[C:23]2[N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[C:9]2[C:14](=[CH:15][C:16]=1[Cl:17])[N:13]=[C:12]([O:18][CH3:19])[C:11]([O:20][CH3:21])=[N:10]2

Participants

3

Reactant 2

HCID 795ImidazoleHCID 22614841HCID 22614841, compound

Product 1

HCID 22614895HCID 22614895, compoundYield 32.1%

Conditions

Temperature
100 °C

Procedure

A mixture of imidazole (78 mg, 1.15 mmol) and 6,7-dichloro-2,3-dimethoxy-5-(3-bromo-5-methyl-4H-1,2,4-triazol-4-yl)quinoxaline (48 mg, 0.115 mmol) was heated at 100° C. for 1 hour then at 120° C. for 3 hours. After being cooled the mixture was partitioned between water (15 mL) and dichloromethane (2×15 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using dichloromethane:methanol (98:2 changing to 95:5, by volume) to give the title compound (15 mg, 32%) as a brown solid.

Workup

  1. temperatureAfter being cooled the mixture
  2. customwas partitioned between water (15 mL) and dichloromethane (2×15 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel, by gradient elution

Sources & evidence

ORD record
ord-df90463f98604b69ae16b432d7ad001f
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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