Triethylamine → HCID 57786131, compound

HRID 1399153Notes

Reaction equation

HRID 1399153 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]([CH2:14][CH2:15][CH2:16]O)[C:12]3[C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:20]=[C:21]([Cl:22])[C:11]=3[N:10]=2)=[C:4]([Cl:27])[CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3=[N:10][C:11]4[C:12](=[C:18]([C:23]([O:25][CH3:26])=[O:24])[CH:19]=[CH:20][C:21]=4[Cl:22])[N:13]3[CH2:14][CH2:15][CH2:16]2)=[C:4]([Cl:27])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 68763449HCID 68763449, compound

Product 1

HCID 57786131HCID 57786131, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[(4-bromo-2-chlorophenyl)amino]-4-chloro-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylate (9.08 g, 19.20 mmol) in tetrahydrofuran (90.0 mL) were added triethylamine (13.4 mL, 96.00 mmol) and methanesulfonyl chloride (5.94 mL, 76.80 mmol) at 0° C. The reaction mixture was stirred at room temperature for 3.5 hrs. The mixture was quenched with aqueous sodium hydrogen carbonate and extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The resulting mesylate was dissolved into N,N-dimethylformamide (50.0 mL) and to the solution was added potassium carbonate (5.31 g, 38.40 mmol). The mixture was stirred at 60° C. for 17 hrs. After cooling, the mixture was diluted with water. The generated precipitate was collected by filtration and washed with diisopropyl ether/ethyl acetate to give the title compound as a colorless solid (7.60 g, 16.70 mmol, 87%).

Workup

  1. customThe mixture was quenched with aqueous sodium hydrogen carbonate
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with brine (×1)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting mesylate was dissolved into N,N-dimethylformamide (50.0 mL) and to the solution
  8. stirringThe mixture was stirred at 60° C. for 17 hrs
  9. temperatureAfter cooling
  10. filtrationThe generated precipitate was collected by filtration
  11. washwashed with diisopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-6c79337106494c18a627e8cfe412f5b2
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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