Imidazole → HCID 19592333, compound

HRID 613543Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:17][C:18](=[O:27])[C:19]1[C:24](Cl)=[CH:23][CH:22]=[CH:21][C:20]=1Cl.[NH:28]1[CH:32]=[CH:31][N:30]=[CH:29]1.C(=O)([O-])[O-].[K+].[K+]>[Cu-]=O.CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:17][C:18](=[O:27])[C:19]1[C:24]([N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)=[CH:23][CH:22]=[CH:21][C:20]=1[N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 3-bromo-8-(2,6-dichlorobenzoylamino)-4-(imidazol-1-yl)quinoline (50 mg) and N-methylpyrrolidone were added imidazole (11 mg), potassium carbonate (22.4 mg) and copper(I) oxide (7.74 mg), and the mixture was stirred for 1.5 hours at 60° C. and for 1 hour at 80° C. The mixture was partitioned between dichloromethane and water, and the organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography and crystallized from diisopropyl ether to give 3-bromo-8-[2,6-bis(imidazol-1-yl)benzoylamino]-4-(imidazol-1-yl)quinoline (17 mg).

Workup

customThe mixture was partitioned between dichloromethane and water
washthe organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by preparative thin layer chromatography
customcrystallized from diisopropyl ether

Sources & evidence

ORD record: ord-75f9d5834e8f4cf58ffdefd7fcf3c313
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008230

Reaction notes

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