Hydrochloric Acid → (2-{3-fluoro-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid

HRID 1960561Notes

Reaction equation

HRID 1960561 reaction equation
[F:1][C:2]1[C:10]2[C:5](=[C:6]([N:11]([CH3:20])[S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:21]1[S:22][CH:23]([CH2:26][C:27]([O:29]CC)=[O:28])[CH2:24][N:25]=1.[OH-].[Na+].Cl>O1CCCC1.C(O)C>[F:1][C:2]1[C:10]2[C:5](=[C:6]([N:11]([CH3:20])[S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:13])=[O:14])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:21]1[S:22][CH:23]([CH2:26][C:27]([OH:29])=[O:28])[CH2:24][N:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86619910HCID 86619910, compound

Product 1

HCID 59135752(2-{3-fluoro-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acidYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (2-{3-fluoro-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (0.1 g) in tetrahydrofuran (1 mL) and ethanol (1 mL) was added 2N aqueous sodium hydroxide solution (0.15 mL), and the mixture was stirred at room temperature for 1 hr, and then at 50° C. for 1 hr. The mixture was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried (MgSO4), and concentrated. The obtained residue was recrystallized from ethyl acetate to give the title compound (0.080 g, yield 85%) as colorless crystals. melting point 213-214° C.

Workup

  1. waitat 50° C. for 1 hr
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-92f705805fb045f18bb89da368a31af8
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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