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

HRID 1960518Notes

Reaction equation

HRID 1960518 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][S:6][CH2:7][CH2:8][CH:9]1[S:13][C:12]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[N:23]([CH3:32])[S:24]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)(=[O:26])=[O:25])=[N:11][CH2:10]1)C.[OH-].[K+].Cl>O1CCCC1.CO.O>[CH3:32][N:23]([S:24]([C:27]1[S:28][CH:29]=[CH:30][CH:31]=1)(=[O:26])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:16]=1[NH:15][C:14]([C:12]1[S:13][CH:9]([CH2:8][CH2:7][S:6][CH2:5][C:4]([OH:33])=[O:3])[CH2:10][N:11]=1)=[CH:22]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59136154ethyl{[2-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)ethyl]thio}acetate

Product 1

HCID 59135892{[2-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)ethyl]thio}acetic acidYield 61.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl{[2-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)ethyl]thio}acetate (60 mg) in tetrahydrofuran (2 mL) and methanol (2 mL) was added, under ice-cooling, a solution prepared by dissolving potassium hydroxide (purity 85%, 20 mg) in water (0.5 mL). The reaction mixture was allowed to warm to room temperature, and stirred for 1 hr. 1M Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO4), and concentrated. The residue was recrystallized from a mixed solvent of ethyl acetate-hexane to give the title compound (35 mg, yield 61%) as white crystals. MS:496(MH+).

Workup

  1. temperaturecooling
  2. customa solution prepared
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water and saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was recrystallized from a mixed solvent of ethyl acetate-hexane

Sources & evidence

ORD record
ord-86b9330cb7364c458307e4e02079de15
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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