Potassium Carbonate → HCID 57475959, compound

HRID 1960244Notes

Reaction equation

HRID 1960244 reaction equation
COC[N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[NH:13][S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:22]([NH2:24])=[O:23].Br[CH2:26][CH2:27][O:28][CH2:29][CH3:30].C(=O)([O-])[O-].[K+].[K+].O.O.C(O)(=O)C(O)=O>C(OCC)(=O)C.[Cl-].[Na+].O.O.CO.CN(C)C=O>[CH2:27]([O:28][CH2:29][CH2:30][N:13]([S:14]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:16])[C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[NH:4][C:5]([C:22]([NH2:24])=[O:23])=[CH:6]2)[CH3:26]

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 61373Oxalic acid dihydrateHCID 57475954HCID 57475954, compound

Product 1

HCID 57475959HCID 57475959, compoundYield 95%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 1-(methoxymethyl)-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (6.25 g), 1-bromo-2-ethoxyethane (3.41 g), potassium carbonate (7.09 g) and N,N-dimethylformamide (30 ml) was stirred at 75° C. for 6 hr. The reaction mixture was diluted with ethyl acetate and saturated brine. The organic layer was washed with aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated. The obtained residue was subjected to basic silica gel column chromatography, and eluted with ethyl acetate-hexane (2:1) mixture to give a solid. A mixture of this solid (5.50 g), oxalic acid dihydrate (4.77 g), methanol (50 ml) and water (50 ml) was stirred at 90° C. for 14 hr. The reaction mixture was allowed to cool to room temperature, and diluted with water, and the obtained solid was crystallized, and washed with water to give the title compound (4.70 g, yield 95%) as crystals. melting point 135° C.

Workup

  1. washThe organic layer was washed with aqueous sodium bicarbonate and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltrated
  4. concentrationthe filtrate was concentrated
  5. washeluted with ethyl acetate-hexane (2:1) mixture
  6. customto give a solid
  7. stirringwas stirred at 90° C. for 14 hr
  8. temperatureto cool to room temperature
  9. customthe obtained solid was crystallized
  10. washwashed with water

Sources & evidence

ORD record
ord-87725f80c6724ecbad24865530ede307
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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