Hydrochloric Acid → HCID 57786214, compound

HRID 1629008Notes

Reaction equation

HRID 1629008 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]1[C:14]2[C:15]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[C:24]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:27]=1[Cl:33])=O)(C)(C)C.Cl>CO.C(=O)([O-])O.[Na+]>[Cl:33][C:27]1[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:26]=1[C:24]1[C:11]2=[N:12][C:13]3[C:14](=[C:15]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:16]=[CH:17][CH:18]=3)[N:10]2[CH2:9][CH2:8][N:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86632923HCID 86632923, compound

Product 1

HCID 57786214HCID 57786214, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl(2-{2-[(2,4-dichlorophenyl)carbonyl]-7-(diethylamino)-1H-benzimidazol-1-yl}ethyl)carbamate (Reference example 224, 395 mg, 0.781 mmol) and hydrochloric acid (10%, methanol solution, 2 mL) in methanol (2 mL) was stirred at room temperature for 14 h and at 50° C. for 2 h. The mixture was diluted with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture to give a yellow amorphous solid (258 mg, 0.666 mmol, 85%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-2efa972ae30248beb6dbda318102215b
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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