Methanesulfonic Acid → HCID 136365309, compound

HRID 2395362Notes

Reaction equation

HRID 2395362 reaction equation
CS(O)(=O)=O.[NH2:6][N:7]=[CH:8][NH:9][C:10]([C:12]1[NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[CH:23]([OH:24])[CH2:22][CH2:21][C:20]=1[C:19]=23)=[O:11].[CH3:25]S(O)(=O)=O>CO>[NH2:6][N:7]=[CH:8][NH:9][C:10]([C:12]1[NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[CH:23]([O:24][CH3:25])[CH2:22][CH2:21][C:20]=1[C:19]=23)=[O:11]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 136365310HCID 136365310, compound

Product 1

HCID 136365309HCID 136365309, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the N-(aminoiminomethyl)-1,3,4,5-tetrahydro-5-hydroxy-benz[cd]indole-2-carboxamide methanesulfonate (0.13 g, 0.37 mmol) obtained in Example 7, methanesulfonic acid (0.036 g, 0.37 mmol) and methanol (20 ml) was heated under reflux for 2 hours. Subsequently, the reaction mixture was concentrated to a volume of about 5 ml under reduced pressure and a 5% aqueous sodium chloride solution was added to the residue. The resulting mixture was made basic with 28% aqueous ammonia and extracted twice with ethyl acetate, and the extract solution was washed twice with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=96/4) to obtain N-(aminoiminomethyl)-1,3,4,5-tetrahydro-5-methoxy-benz[cd]indole -2-carboxamide (0.11 g). This compound (0.11 g) was treated with a solution of methanesulfonic acid (0.05 g) in tetrahydrofuran (2.5 ml) to obtain N-(aminoimino-methyl)-1,3,4,5-tetrahydro-5-methoxy-benz[cd]indole-2-carboxamide methanesulfonate (0.08 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationSubsequently, the reaction mixture was concentrated to a volume of about 5 ml under reduced pressure
  4. additiona 5% aqueous sodium chloride solution was added to the residue
  5. extractionextracted twice with ethyl acetate
  6. washthe extract solution was washed twice with a 5% aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by a silica gel column chromatography (eluent: chloroform/methanol=96/4)

Sources & evidence

ORD record
ord-75366f45724c44b183444c59d5f4ccd8
Source dataset
uspto-grants-1998_09
Patent number
US05814654

Reaction notes

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