Dimethylacetamide → Ethyl 2-{4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-4-carboxylate

HRID 1851572Notes

Reaction equation

HRID 1851572 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][C:26](=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28].CN(C)C(=O)C>C(OCC)(=O)C>[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]1[S:23][CH:25]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:22]=1)[NH:6]2

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 66144Ethyl bromopyruvateHCID 574760084-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide

Product 1

HCID 136060823Ethyl 2-{4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-4-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of 4-methyl-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (0.50 g), ethyl bromopyruvate (0.36 mL) and N,N-dimethylacetamide (14 ml) was stirred at 100° C. for 3 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 crystals were washed with ethyl acetate-hexane to give the title compound (403 mg, yield 64%) as pale-brown crystals. MS:462 (MH+).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe obtained crystals were washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-19bbbd10ec66467ca5575e7f8eb33338
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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