Dimethylacetamide → HCID 57901794, compound

HRID 1851391Notes

Reaction equation

HRID 1851391 reaction equation
[F: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:24](=[S:26])[NH2:25])[N:6]2[CH2:21][O:22][CH3:23].Br[CH2:28][CH:29](OCC)OCC.CN(C)C(=O)C>C(OCC)(=O)C>[F: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:13])=[O:14])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:24]1[S:26][CH:28]=[CH:29][N:25]=1)[N:6]2[CH2:21][O:22][CH3:23]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 57901724HCID 57901724, compound

Product 1

HCID 57901794HCID 57901794, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of 4-fluoro-1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (0.25 g), 1-bromo-2,2-diethoxyethane (0.24 mL) and N,N-dimethylacetamide (10 ml) was stirred at 90° C. for 7 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=15:85-30:70) to give the title compound (165 mg, yield 62%) as colorless needle crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5db7587ae2bb4b90a06ff7f0647e2df3
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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