Dimethylacetamide → N-methyl-N-[4-methyl-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamide

HRID 1851571Notes

Reaction equation

HRID 1851571 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:20])[S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:21](=[S:23])[NH2:22])[NH:6]2.Br[CH2:25][CH:26](OCC)OCC.CN(C)C(=O)C>C(OCC)(=O)C>[CH3:20][N:11]([C:8]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]2[C:7]=1[NH:6][C:5]([C:21]1[S:23][CH:25]=[CH:26][N:22]=1)=[CH:4]2)[S:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 574760084-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide

Product 1

HCID 57901591N-methyl-N-[4-methyl-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-sulfonamideYield 43%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of 4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (0.20 g), 1-bromo-2,2-diethoxyethane (0.23 mL) and N,N-dimethylacetamide (10 ml) was stirred at 100° C. for 6 hr. The reaction solution was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=25:75-35:65), and the obtained oil was crystallized from ethyl acetate-hexane to give the title compound (92 mg, yield 43%) as pale-yellow prism crystals. melting point 159-160° C.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe obtained oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1fc8b3471dd7433093729c97be2a73e6
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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