Hydrochloric Acid → 2-Fluoro-4-[(1,3-thiazol-2-ylamino)sulfonyl]benzoic acid

HRID 401762Notes

Reaction equation

HRID 401762 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:21]1[S:22][CH:23]=[CH:24][N:25]=1)[S:7]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[C:12]([F:20])[CH:11]=1)(=[O:9])=[O:8].[OH-].[Na+].Cl>C1COCC1.CO.O>[NH3:6].[F:20][C:12]1[CH:11]=[C:10]([S:7]([NH:6][C:21]2[S:22][CH:23]=[CH:24][N:25]=2)(=[O:8])=[O:9])[CH:19]=[CH:18][C:13]=1[C:14]([OH:16])=[O:15]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57732244Methyl 4-{[(2,4-dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}-2-fluorobenzoate

Product 2

HCID 222AmmoniaHCID 577320872-Fluoro-4-[(1,3-thiazol-2-ylamino)sulfonyl]benzoic acidYield 22.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-{[(2,4-dimethoxybenzyl)(1,3-thiazol-2-yl)amino]sulfonyl}-2-fluorobenzoate (Preparation 14, 10 g, 21 mmol, 1 eq) and sodium hydroxide 4.3 g, 0.107 mol, 5 eq) in THF: MeOH: water (25 ml:2 ml:75 ml) was heated at 50° C. for 4 hours. The reaction mixture was acidified to pH 2.0 with 2M HCl and the resulting precipitate collected by filtration. The crude material was purified by column chromatography eluting with 90:10:1 DCM: MeOH: ammonia to yield the title compound as a yellow solid (706 mg, 2.33 mmol, 11%).

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. customThe crude material was purified by column chromatography
  3. washeluting with 90:10:1 DCM

Sources & evidence

ORD record
ord-691ad5f4549a4d5597977683dfe0e305
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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