Methanesulfonic Acid → HCID 178493040, compound

HRID 1700598Notes

Reaction equation

[C:1]([NH:4][NH2:5])([NH2:3])=[NH:2].Cl.[CH3:7][S:8]([OH:11])(=[O:10])=[O:9].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]1[CH2:28][C:27]2[N:26]=[CH:25][CH:24]=[C:23]([O:29][CH3:30])[C:22]=2[C:21](=O)[CH2:20]1>CO>[CH3:7][S:8]([OH:11])(=[O:10])=[O:9].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]1[CH2:28][C:27]2[N:26]=[CH:25][CH:24]=[C:23]([O:29][CH3:30])[C:22]=2[C:21](=[N:5][NH:4][C:1]([NH2:3])=[NH:2])[CH2:20]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of aminoguanidine hydrochloride (0.048 g) in methanol (20 ml) was added methanesulfonic acid (0.042 g), and the mixture was refluxed for 1 hour. To the mixture were added 7-(2-chlorophenyl)-4-methoxy-5,6,7,8-tetrahydroquinolin-5-one (0.12 g) and methanesulfonic acid (0.042 g), and the mixture was stirred at 50° C. for 9 hours and at 60° C. for 16 hours. Under reduced pressure, the solvent was evaporated. To the residue was added water, and the mixture was washed with ethyl acetate. Under reduced pressure, the solvent was evaporated, and the residue was recrystallized from water-ethanol to give 7-(2-chlorophenyl)-5-guanidinoimino-4-methoxy-5,6,7,8-tetrahydroquinoline methanesulfonate (Compound 79) (0.19 g) as colorless crystals.

Workup

temperaturethe mixture was refluxed for 1 hour
customUnder reduced pressure, the solvent was evaporated
additionTo the residue was added water
washthe mixture was washed with ethyl acetate
customUnder reduced pressure, the solvent was evaporated
customthe residue was recrystallized from water-ethanol

Sources & evidence

ORD record: ord-7569e7388a9543f0b1e84c0758386150
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350749B1

Reaction notes

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