Methanesulfonic Acid → HCID 178511924, compound

HRID 1419250Notes

Reaction equation

HRID 1419250 reaction equation
CS(O)(=O)=O.[NH2:6][N:7]=[CH:8][NH:9][C:10]1[CH:36]=[CH:35][C:13]([C:14]([O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:27](=[NH:29])[NH2:28])[CH:23]=3)[C:18]=2[CH2:30][C:31]([O:33]C)=[O:32])=[O:15])=[CH:12][CH:11]=1>>[NH2:6][N:7]=[CH:8][NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:27](=[NH:28])[NH2:29])[CH:23]=3)[C:18]=2[CH2:30][C:31]([OH:33])=[O:32])=[O:15])=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178499606HCID 178499606, compound

Product 1

HCID 178511924HCID 178511924, compoundYield 24%

Conditions

Temperature
60 °C

Procedure

30 Milliliters of 20% aqueous methanesulfonic acid solution was added to 2.5 g of 6-amidino-1-methoxycarbonylmethyl-2-naphthyl 4-aminoiminomethylaminobenzoate.dimethanesulfonate, followed by stirring for 3 hours at 60° C. Then, 700 mg of active carbon was added to the reaction mixture, followed by stirring for 30 minutes at room temperature. Insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. To the residue was added 30 ml of water to dissolve the residue. The solution was added dropwise to 150 ml of acetone, followed by stirring for 1 hour under cooling with ice. Then, the precipitate was collected by filtration and washed with a small amount of acetone to obtain 580 mg of the desired product.

Workup

  1. additionThen, 700 mg of active carbon was added to the reaction mixture
  2. stirringby stirring for 30 minutes at room temperature
  3. filtrationInsoluble matter was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the residue was added 30 ml of water
  6. dissolutionto dissolve the residue
  7. additionThe solution was added dropwise to 150 ml of acetone
  8. stirringby stirring for 1 hour
  9. temperatureunder cooling with ice
  10. filtrationThen, the precipitate was collected by filtration
  11. washwashed with a small amount of acetone

Sources & evidence

ORD record
ord-f0f61247e4d44922b74b2358136565ae
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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