Methanol → 4-[4-[(6-Fluoro-1,3-benzothiazol-2-yl)amino]phenyl]benzoic acid

HRID 2356804Notes

Reaction equation

[F:1][C:2]1[CH:27]=[CH:26][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])=[CH:18][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:27]=[CH:26][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])=[CH:18][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]biphenyl-4-carboxylate (94 mg, 0.25 mmol) was suspended in THF (3 mL), MeOH (3 mL), and water (1.5 mL), and NaOH (0.10 g, 2.5 mmol) was added. The reaction mixture was heated at 50° C. for 3 h. Upon cooling to rt, the reaction mixture was concentrated in vacuo, acidified with 2N HCl, and the resulting solid was collected by filtration. This yielded 90 mg (99%) of the title compound. LC/MS m/z 365.2 (MH+), retention time 3.46 min. 1H NMR (400 MHz, DMSO-d6) δ 7.08 (t, 1H), 7.49-7.80 (m, 6H), 7.82-8.01 (m, 4H), 10.75 (br, 1H).

Workup

temperatureUpon cooling to rt
concentrationthe reaction mixture was concentrated in vacuo
filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record: ord-5a5aa749493c4794ae2221bb2fb60c3a
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759376B2

Reaction notes

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