Methanol → HCID 59385247, compound

HRID 2356805Notes

Reaction equation

HRID 2356805 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])=[C:21]([O:29][CH3:30])[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.O.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:27])=[O:26])=[C:21]([O:29][CH3:30])[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

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 59385246HCID 59385246, compound

Product 1

HCID 59385247HCID 59385247, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3′-fluoro-4′-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-3-methoxybiphenyl-4-carboxylate (0.43 g, 1.01 mmol) was suspended in THF (10 mL), MeOH (5 mL) and water (5 mL), and NaOH (0.40 g, 10 mmol) was added. The reaction mixture was stirred at rt for 18 h. The reaction mixture was concentrated under reduced pressure, acidified with 2N HCl, and the resulting solid was collected by filtration. This yielded 0.41 g (99%) of the title compound as a light brown solid. LC/MS m/z 413.3 (MH+), retention time 3.44 min. 1H NMR (400 MHz, DMSO-d6) δ 3.91 (s, 3H), 7.17 (t, 1H), 7.24-7.29 (m, 2H), 7.58-7.78 (m, 5H), 8.63 (t, 1H), 10.45 (br, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-8db3745d3a0a424c9b393cfafcadc29f
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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