Water → HCID 57901629, compound

HRID 1851587Notes

Reaction equation

HRID 1851587 reaction equation
Cl[CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[S:8]([N:11]([CH3:26])[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][CH:23]=[CH:24][N:25]=1)=[CH:17]2)(=[O:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[SH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36].O>CN(C)C=O>[CH3:26][N:11]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]1[S:22][CH:23]=[CH:24][N:25]=1)=[CH:17]2)[S:8]([C:7]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:2][S:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 57901769HCID 57901769, compound

Product 1

HCID 57901629HCID 57901629, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(chloromethyl)-N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-3-sulfonamide (450 mg) in N,N-dimethylformamide (5 mL) were added potassium carbonate (150 mg) and methyl mercaptoacetate (130 μL), and the mixture was stirred at 50° C. for 10 hr. Water 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 obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (348 mg, yield 67%) as pale-yellow crystals. melting point 126° 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-c819123656e3459485f8fa31927be144
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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