Hydrochloric Acid → HCID 68461826, compound

HRID 1960534Notes

Reaction equation

HRID 1960534 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:15][C:14]=3[N:25]([CH3:35])[S:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)(=[O:28])=[O:27])=[N:8][CH2:7]1)C.[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH3:24][O:23][CH2:22][CH2:21][O:20][C:16]1[CH:17]=[C:18]2[C:13](=[C:14]([N:25]([CH3:35])[S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)(=[O:28])=[O:27])[CH:15]=1)[NH:12][C:11]([C:9]1[S:10][CH:6]([CH2:5][C:4]([OH:36])=[O:3])[CH2:7][N:8]=1)=[CH:19]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59303547HCID 59303547, compound

Product 1

HCID 68461826HCID 68461826, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl(2-{5-(2-methoxyethoxy)-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (960 mg), 1N aqueous sodium hydroxide solution (5 mL), tetrahydrofuran (5 mL) and ethanol (5 mL) was stirred for 50° C. for 1 hr. 1N Hydrochloric acid (5 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated to give the title compound (800 mg, yield 88%) as a yellow amorphous solid. The solid was crystallized from ethyl acetate-hexane, and recrystallized from ethyl acetate-hexane to give pale-yellow powder. melting point 107-109° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-56d7edf4bfa949f1b23b0749990a2cec
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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