Ethyl ketone → HCID 66743818, compound

HRID 2363959Notes

Reaction equation

HRID 2363959 reaction equation
[CH3:1][NH:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[C:14]([NH2:16])=[O:15].[CH3:17][CH2:18][C:19](=O)[CH2:20][CH3:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:18]([C:19]1([CH2:20][CH3:21])[N:2]([CH3:1])[C:3]2[CH:7]=[C:6]([C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)[S:5][C:4]=2[C:14](=[O:15])[NH:16]1)[CH3:17]

Participants

6

Reactant 4

HCID 7288Ethyl ketoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 66743384HCID 66743384, compound

Product 1

HCID 66743818HCID 66743818, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-(methylamino)-5-(pyridin-4-yl)thiophene-2-carboxamide (0.094 g, 0.40 mmol), 3-pentanone (2.5 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred for 1 h at 120° C. in a sealed tube. Then, this mixture was stirred for 1.5 h at 150° C. in a sealed tube. The mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate (100 mL), drying over magnesium sulfate, filtration and concentration at reduced pressure gave an oil. This oil was purified by column chromatography (Combiflash, 40 g silica gel, dichloromethane to 95:5 dichloromethane/methanol), then triturated with ethyl acetate/hexanes (1:1), and the precipitate was collected by filtration to afford the title compound (0.0281 g, 23%) as a yellow solid:

Workup

  1. stirringThen, this mixture was stirred for 1.5 h at 150° C. in a sealed tube
  2. extractionExtraction with ethyl acetate (100 mL)
  3. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  4. customgave an oil
  5. customThis oil was purified by column chromatography (Combiflash, 40 g silica gel, dichloromethane to 95:5 dichloromethane/methanol)
  6. customtriturated with ethyl acetate/hexanes (1:1)
  7. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-d601ea64ddbb4fd9a6dc3faab5f36b11
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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