Methanesulfonic Acid → HCID 178493039, compound

HRID 1700597Notes

Reaction equation

[C:1]([NH:4][NH2:5])([NH2:3])=[NH:2].Cl.[CH3:7][S:8]([OH:11])(=[O:10])=[O:9].[CH3:12][O:13][C:14]1[C:23]2[C:22](=O)[CH2:21][CH:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][C:18]=2[N:17]=[CH:16][CH:15]=1>C(O)C>[CH3:7][S:8]([OH:11])(=[O:10])=[O:9].[NH:4]([N:5]=[C:22]1[CH2:21][CH:20]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:19][C:18]2[N:17]=[CH:16][CH:15]=[C:14]([O:13][CH3:12])[C:23]1=2)[C:1]([NH2:3])=[NH:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of aminoguanidine hydrochloride (0.023 g) in ethanol (10 ml) was added methanesulfonic acid (0.02 g), and the mixture was refluxed for 30 minutes. To the solution was added 4-methoxy-7-phenyl-5,6,7,8-tetrahydroquinolin-5-one (0.05 g), and the mixture was stirred at room temperature for 2 hours and 20 minutes and at 50° C. for 25 minutes. To the mixture was added methanesulfonic acid (0.02 g), and the mixture was stirred at 50° C. for 5 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in water. The solution was washed with ethyl acetate. Under reduced pressure, the solvent was evaporated, and the residue was recrystallized from ethanol-water to give 5-guanidinoimino-4-methoxy-7-phenyl-5,6,7,8-tetrahydroquinoline methanesulfonate (Compound 78) (0.09 g) as colorless crystals.

Workup

temperaturethe mixture was refluxed for 30 minutes
stirringthe mixture was stirred at 50° C. for 5 hours
customUnder reduced pressure, the solvent was evaporated
dissolutionthe residue was dissolved in water
washThe solution was washed with ethyl acetate
customUnder reduced pressure, the solvent was evaporated
customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record: ord-1691a1fd8bb54385a7c14bdb37ac3354
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350749B1

Reaction notes

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