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O-Xylene → 8-Chloro-1-[6-(dimethylamino)-4-methylpyridin-3-yl]-5-(1-ethylpropyl)-1H-imidazo[1,2-a]benzimidazol-2(3H)-one

HRID 1398968
Notes
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Reaction equation

HRID 1398968 reaction equation
Cl[C:2]1[N:6]([CH2:7][C:8]([O:10]C(C)C)=O)[C:5]2[C:14]([CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][CH:16]=[C:17]([Cl:18])[C:4]=2[N:3]=1.[CH3:24][N:25]([CH3:34])[C:26]1[CH:31]=[C:30]([CH3:32])[C:29]([NH2:33])=[CH:28][N:27]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C(C)=CC=CC=1>O>[Cl:18][C:17]1[C:4]2[N:3]=[C:2]3[N:33]([C:29]4[CH:28]=[N:27][C:26]([N:25]([CH3:24])[CH3:34])=[CH:31][C:30]=4[CH3:32])[C:8](=[O:10])[CH2:7][N:6]3[C:5]=2[C:14]([CH:19]([CH2:20][CH3:21])[CH2:22][CH3:23])=[CH:15][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 521998p-Toluenesulfonic acid monohydrateHCID 22136281N2,N2,4-trimethylpyridine-2,5-diamineHCID 86632857Isopropyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate

Product 1

HCID 577859208-Chloro-1-[6-(dimethylamino)-4-methylpyridin-3-yl]-5-(1-ethylpropyl)-1H-imidazo[1,2-a]benzimidazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of isopropyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate (Reference Example 10; 1.62 g, 4.53 mmol), N2,N2,4-trimethylpyridine-2,5-diamine (2.06 g, 4.85 mmol), p-toluenesulfonic acid monohydrate (922.9 mg, 4.85 mmol) and xylene (8.0 mL) was stirred at 150° C. for 3 days. After cooling, the reaction mixture was diluted with water and the resulting precipitate was removed by filtration. The filtrate was extracted with ethyl acetate (×3). The combined organic layer was washed with 1N hydrochloric acid (×2) and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 0-15% ethyl acetate/n-hexane gradient mixture to give a mixture containing the title compound. The residue was purified by preparative HPLC to give the title compound as the trifluoroacetic acid salt. The salt was washed with aqueous saturated sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting solid was recrystallized from n-hexane to give the title compound as a colorless powder (49.7 mg, 0.121 mmol, 2.7%).

Workup

  1. temperatureAfter cooling
  2. customthe resulting precipitate was removed by filtration
  3. extractionThe filtrate was extracted with ethyl acetate (×3)
  4. washThe combined organic layer was washed with 1N hydrochloric acid (×2) and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a 0-15% ethyl acetate/n-hexane gradient mixture
  10. customto give a mixture

Sources & evidence

ORD record
ord-cec90efbe39f43fe9b0c37f0a87d51d6
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08901141B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes