Methanesulfonic Acid → 6-amidino-1-carboxymethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]-benzoate

HRID 1419248Notes

Reaction equation

HRID 1419248 reaction equation
CS(O)(=O)=O.[NH:6]1[CH2:10][CH2:9][N:8]=[C:7]1[NH:11][C:12]1[CH:38]=[CH:37][C:15]([C:16]([O:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:29](=[NH:31])[NH2:30])[CH:25]=3)[C:20]=2[CH2:32][C:33]([O:35]C)=[O:34])=[O:17])=[CH:14][CH:13]=1>>[NH:8]1[CH2:9][CH2:10][N:6]=[C:7]1[NH:11][C:12]1[CH:38]=[CH:37][C:15]([C:16]([O:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:29](=[NH:30])[NH2:31])[CH:25]=3)[C:20]=2[CH2:32][C:33]([OH:35])=[O:34])=[O:17])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 867539746-amidino-1-methoxycarbonylmethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]benzoate

Product 1

HCID 867539756-amidino-1-carboxymethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]-benzoateYield 48.8%

Conditions

Temperature
80 °C

Procedure

45 Milliliters of 10% aqueous methanesulfonic acid solution was added to 500 mg of 6-amidino-1-methoxycarbonylmethyl-2-naphthyl 4-[(4,5-dihydro-1H-imidazol-2-yl)amino]benzoate.dimethanesulfonate, followed by stirring for 5 hours at 80° C. After leaving the mixture for cooling, 350 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 a small amount of water. The solution was added dropwise to a mixed liquid of 150 ml of acetone and 50 ml of ether, 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 236.1 mg of the desired product.

Workup

  1. customAfter leaving the mixture
  2. temperaturefor cooling
  3. addition350 mg of active carbon was added to the reaction mixture
  4. stirringby stirring for 30 minutes at room temperature
  5. filtrationInsoluble matter was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionTo the residue was added a small amount of water
  8. additionThe solution was added dropwise to a mixed liquid of 150 ml of acetone and 50 ml of ether
  9. stirringby stirring for 1 hour
  10. temperatureunder cooling with ice
  11. filtrationThen, the precipitate was collected by filtration
  12. washwashed with a small amount of acetone

Sources & evidence

ORD record
ord-a853fd221396422ea8a889b6c46edb0e
Source dataset
uspto-grants-1999_03
Patent number
US05885990

Reaction notes

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