Hydrochloric Acid → HCID 57901578, compound

HRID 1851396Notes

Reaction equation

HRID 1851396 reaction equation
COC[N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]([CH3:26])S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)[CH:6]=[C:5]1[C:27]([O:29][CH2:30][CH3:31])=[O:28].Cl>C(O)C>[CH3:26][NH:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[NH:4][C:5]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:6]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57901774HCID 57901774, compound

Product 1

HCID 57901578HCID 57901578, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 1-(methoxymethyl)-7-{methyl[(4-nitrophenyl)sulfonyl]amino}-1H-indole-2-carboxylate (1.42 g) in ethanol (10 mL) was added 6N hydrochloric acid (10 mL), and the mixture was stirred at 70° C. for 12 hr. The reaction mixture was concentrated, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was dissolved in N,N-dimethylformamide (8 mL), lithium hydroxide (520 mg) and mercaptoacetic acid (430 μL) were added, and the mixture was stirred at room temperature for 12 hr. To the reaction mixture was added methyl iodide (100 μL), and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give a yellow amorphous (182 mg, yield 26%). M+1=219.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (8 mL)
  8. additionlithium hydroxide (520 mg) and mercaptoacetic acid (430 μL) were added
  9. stirringthe mixture was stirred at room temperature for 12 hr
  10. additionTo the reaction mixture was added methyl iodide (100 μL)
  11. stirringthe mixture was stirred at room temperature for 1 hr
  12. additionSaturated aqueous sodium hydrogencarbonate solution was added to the reaction solution
  13. extractionthe mixture was extracted with ethyl acetate
  14. washThe ethyl acetate layer was washed with saturated brine
  15. dry with materialdried (MgSO4)
  16. concentrationconcentrated
  17. customto give a yellow amorphous (182 mg, yield 26%)

Sources & evidence

ORD record
ord-c75fe21bba54427089fd445f0f4165c9
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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