Citric Acid → 5-methyl-2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl)-4,5-dihydro-1,3-thiazole-5-carboxylic acid

HRID 1994743Notes

Reaction equation

HRID 1994743 reaction equation
C(C1(C)[S:7][C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[N:17]([CH3:26])[S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])=[N:5]C1)#N.[OH-].[Na+].O1CCCC1.C(O)(=O)[CH2:36][C:37]([CH2:42]C(O)=O)([C:39]([OH:41])=[O:40])O>C(O)C>[CH3:42][C:37]1([C:39]([OH:41])=[O:40])[S:7][C:6]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[N:17]([CH3:26])[S:18]([C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)(=[O:20])=[O:19])=[N:5][CH2:36]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59135902N-[2-(5-cyano-5-methyl-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide

Product 1

HCID 574761205-methyl-2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl)-4,5-dihydro-1,3-thiazole-5-carboxylic acidYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[2-(5-cyano-5-methyl-4,5-dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide (0.15 g), 2N aqueous sodium hydroxide solution (0.36 ml), tetrahydrofuran (3 ml) and ethanol (3 ml) was heated under reflux for 4 hr. 10% Aqueous citric acid solution 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. The residue was subjected to silica gel column chromatography to give the title compound (0.11 g, yield 69%) as yellow crystals from a fraction eluted with tetrahydrofuran. melting point >232° C. (decomposition).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9270da9677ff408bacb40fcce97628b0
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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