8-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl)amino]benzyloxy]-2-methylquinoline → Sulfuric Acid

HRID 564958Notes

Reaction equation

[Cl:1][C:2]1[C:20]([N:21]([CH3:40])[C:22](=[O:39])[CH2:23][NH:24][C:25](=[O:38])[CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([C:34](=[O:37])[NH:35][CH3:36])=[CH:30][CH:29]=2)=[CH:19][CH:18]=[C:17]([Cl:41])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.[S:42](=[O:46])(=[O:45])([OH:44])[OH:43].C(O)C>C(O)C>[S:42](=[O:44])(=[O:43])([OH:46])[OH:45].[Cl:1][C:2]1[C:20]([N:21]([CH3:40])[C:22](=[O:39])[CH2:23][NH:24][C:25](=[O:38])[CH:26]=[CH:27][C:28]2[CH:29]=[CH:30][C:31]([C:34](=[O:37])[NH:35][CH3:36])=[CH:32][CH:33]=2)=[CH:19][CH:18]=[C:17]([Cl:41])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 8-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl)amino]benzyloxy]-2-methylquinoline (225 mg) in ethanol (2.3 ml) was added 1N sulfuric acid-ethanol solution (0.38 ml) at ambient temperature, and the mixture was warmed at 90° C. and then stirred for 1 hour at ambient temperature. The resulting precipitate was collected by filtration, and the residue was dissolved in methylene chloride-methanol (10:1). The solvent was removed in vacuo to give ½ sulfuric acid salt of 8-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-2-methylquinoline (210 mg).

Workup

filtrationThe resulting precipitate was collected by filtration
dissolutionthe residue was dissolved in methylene chloride-methanol (10:1)
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-4c785685bbbd4aaca05fa80c9c560ba5
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169095A

Reaction notes

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