Hydrochloric Acid → 4-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-7-trifluoromethylquinoline-3-carboxylic acid

HRID 2300241Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[N:16]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[CH:13][CH:12]=[C:11]([C:35]([F:38])([F:37])[F:36])[CH:10]=2)=[O:5])C.[OH-].[Na+].Cl>CO.C1COCC1>[CH2:28]([N:16]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:15]1[C:14]2[C:9](=[CH:10][C:11]([C:35]([F:37])([F:38])[F:36])=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 1.065 g (2.00 mmol) of the product from Example 1 in 4 mL of methanol/THF (1:1) was added 2 mL of 1N sodium hydroxide solution and the resulting mixture was stirred at 25° C. for 18 h. The reaction was then acidified with 1N HCl and extracted with ethyl acetate (200 mL). The organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was triturated with ethyl acetate/hexane (1:9) and filtered to provide 828 mg (82%) of the desired carboxylic acid as a white solid. Electrospray Mass Spec 517.1 (M+H)

Workup

extractionextracted with ethyl acetate (200 mL)
washThe organic layer was washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was triturated with ethyl acetate/hexane (1:9)
filtrationfiltered

Sources & evidence

ORD record: ord-78767e37c922479fbda2bf40dbaf8ad7
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498167B2

Reaction notes

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