HCID 44156374, compound → 9-Chloro-1-(2,4-dichlorophenyl)-6-[1-(1H-imidazol-1-yl) propyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

HRID 1628700Notes

Reaction equation

HRID 1628700 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23](O)[CH2:24][CH3:25])=[CH:4][CH:3]=1>ClCCl>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=4[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:23]([N:7]2[CH:6]=[CH:10][N:9]=[CH:8]2)[CH2:24][CH3:25])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 44156374HCID 44156374, compound

Product 1

HCID 577857799-Chloro-1-(2,4-dichlorophenyl)-6-[1-(1H-imidazol-1-yl) propyl]-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazoleYield 187.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-ol (150 mg, 0.326 mmol) and N,N′-carbonyldiimidazole (119 mg, 0.734 mmol) in dichloromethane (2.0 mL) was stirred at 50° C. for 22 hr. The mixture was concentrated in vacuo, diluted with 1N hydrochloric acid and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/n-hexane to give the title compound as a colorless crystal (141 mg, 0.306 mmol, 94%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additiondiluted with 1N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture
  9. concentrationThe filtrate was concentrated in vacuo
  10. customto give the solid, which
  11. customwas recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-08b1b2245cb84d8c806373ec60dc4259
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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