Methanol → 4'-[(6-Fluoro-1,3-benzothiazol-2-yl)amino]-3-chlorobiphenyl-4-carboxylic acid

HRID 2356811Notes

Reaction equation

[F:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=[O:23])=[C:18]([Cl:26])[CH:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.CO.O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[C:18]([Cl:26])[CH:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Methyl 4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-chlorobiphenyl-4-carboxylate (0.30 g, 0.71 mmol) was suspended in THF (5 mL), MeOH (5 mL) and water (2.5 mL), and then NaOH (0.28 g, 7.1 mmol) was added. The reaction mixture was heated at 50° C. for 3 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure, acidified, and the resulting solid was collected by filtration. This yielded 0.34 g (quantitative) of the title compound. LC/MS m/z 399.2 (MH+), retention time 3.53 min.

Workup

temperatureUpon cooling to rt
concentrationthe reaction mixture was concentrated under reduced pressure
filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record: ord-f70a7edf0e7c47a9b12879a2ab8c0c5c
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759376B2

Reaction notes

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