Triethylamine → 8-Chloro-1-[(6-chloropyridin-3-yl)carbonyl]-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

HRID 1399141Notes

Reaction equation

HRID 1399141 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[NH:11][CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][N:28]=1>O1CCCC1.O>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:31]([C:30]4[CH:29]=[N:28][C:27]([Cl:26])=[CH:35][CH:34]=4)=[O:32])[CH2:12][CH2:13][N:7]3[C:6]=2[C:5]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27821656-Chloronicotinoyl ChlorideHCID 1360477328-Chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole

Product 1

HCID 577862568-Chloro-1-[(6-chloropyridin-3-yl)carbonyl]-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazoleYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 8-chloro-5-(1-ethylpropyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole (31.2 mg, 0.118 mmol) in tetrahydrofuran (0.5 mL) were added triethylamine (19.8 μL, 0.142 mmol) and 6-chloronicotinoyl chloride (25.0 mg, 0.142 mmol). The reaction mixture was stirred at room temperature for 4 hrs. The mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-30% ethyl acetate/n-hexane gradient mixture. The resulting solid was recrystallized from n-hexane to give the title compound as a colorless powder (27.1 mg, 0.0672 mmol, 57%).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe combined organic layer was washed with brine (×1)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluting with a 0-30% ethyl acetate/n-hexane gradient mixture
  7. customThe resulting solid was recrystallized from n-hexane

Sources & evidence

ORD record
ord-0168a1319856447e918ee402ad97b473
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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