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

HRID 2356807Notes

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]([CH3:26])[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]([CH3:26])[CH:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

As shown in Reaction Scheme 7, methyl 4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methylbiphenyl-4-carboxylate (0.25 g, 0.65 mmol) was suspended in THF (5 mL), MeOH (5 mL) and water (2.5 mL), and NaOH (0.26 g, 6.5 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 0.25 g (quantitative) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 2.62 (s, 3H), 7.05 (t, 1H), 7.57-7.90 (m, 9H), 10.62 (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-5f37c211d6ca4f21b498c2dbbe32c4d6
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759376B2

Reaction notes

Loading…