Dimethylacetamide → HCID 57901714, compound

HRID 1851567Notes

Reaction equation

HRID 1851567 reaction equation
Cl[CH2:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[N:14]([CH3:23])[S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16])=O.[C:24]([NH2:27])(=[S:26])[CH3:25].CN(C)C(=O)C>C(OCC)(=O)C>[CH3:23][N:14]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][C:5]([C:3]1[N:27]=[C:24]([CH3:25])[S:26][CH:2]=1)=[CH:13]2)[S:15]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 2723949ThioacetamideHCID 57901842HCID 57901842, compound

Product 1

HCID 57901714HCID 57901714, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixed solution of N-[2-(2-chloroacetyl)-1H-indol-7-yl]-N-methylthiophene-2-sulfonamide (570 mg), thioacetamide (0.20 g) and N,N-dimethylacetamide (15 ml) was stirred at 80° C. for 2 hr. The reaction solution was diluted with ethyl acetate, washed with water, aqueous sodium hydrogencarbonate solution 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=1:9-4:6), the obtained crude product was purified by preparative HPLC, and the obtained oil was crystallized from ethyl acetate-hexane to give the title compound (64 mg, yield 11%) as colorless needle crystals. melting point 161-162° C. MS:390 (MH+).

Workup

  1. washwashed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe obtained crude product
  5. customwas purified by preparative HPLC
  6. customthe obtained oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a2c971f5cdb14f2aa99f4aead328aa0a
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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