Hydrochloric Acid → HCID 7147096, compound

HRID 2356800Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27]C)=[O:26])=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.CO.[Li+].[OH-].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

As shown in Reaction Scheme 5, methyl 3′-fluoro-4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]biphenyl-4-carboxylate (0.64 g, 1.6 mmol) was suspended in THF (10 mL), MeOH (10 mL) and water (5 mL), and LiOH (0.39 g, 16.2 mmol) was added. The reaction mixture was heated at 50° C. until dissolution was achieved, and then the mixture was stirred for 3 days at rt. The reaction mixture was brought to pH 4 with 1N HCl and was extracted with EtOAc (3×25 mL). The combined organic phases were washed with water (2×50 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated in vacuo. This yielded 0.518 g (84%) of the desired product as an off-white solid. LC/MS m/z 383.3 (MH+), retention time 3.83 min. 1H NMR (400 MHz, DMSO-d6) δ 7.18 (t, 1H), 7.59-8.00 (m, 8H), 8.70 (t, 1H), 10.50 (bs, 1H), 12.95 (bs, 1H).

Workup

extractionwas extracted with EtOAc (3×25 mL)
washThe combined organic phases were washed with water (2×50 mL) and brine (50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-0f773db221744e1d9a4c095fd34e1ad7
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759376B2

Reaction notes

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