3-Hexanone → HCID 66743176, compound

HRID 2363963Notes

Reaction equation

HRID 2363963 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[S:4][C:3]=1[C:13]([NH2:15])=[O:14].[CH3:16][CH2:17][C:18](=O)[CH2:19][CH2:20][CH3:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:17]([C:18]1([CH2:19][CH2:20][CH3:21])[NH:1][C:2]2[CH:6]=[C:5]([C:7]3[CH:8]=[CH:9][N:10]=[CH:11][CH:12]=3)[S:4][C:3]=2[C:13](=[O:14])[NH:15]1)[CH3:16]

Participants

6

Reactant 4

HCID 115093-HexanoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 66743176HCID 66743176, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.108 g, 0.500 mmol), 3-hexanone (2.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (2.0 mL) was stirred overnight at 80° 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, 12 g silica gel, dichloromethane to 90:10 dichloromethane/methanol), then recrystallized from methanol, and the precipitate was collected by filtration. This yellow solid contained methanol, so it was stirred in ethyl acetate (5.0 mL) for 30 min at 70° C. After cooling, the precipitate was collected by filtration to afford the title compound (0.0334 g, 22%) as a yellow solid:

Workup

  1. extractionExtraction with ethyl acetate (100 mL)
  2. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  3. customgave an oil
  4. customThis oil was purified by column chromatography (Combiflash, 12 g silica gel, dichloromethane to 90:10 dichloromethane/methanol)
  5. customrecrystallized from methanol
  6. filtrationthe precipitate was collected by filtration
  7. stirringso it was stirred in ethyl acetate (5.0 mL) for 30 min at 70° C
  8. temperatureAfter cooling
  9. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-db4b1a7c2e044449810d619f56de77a6
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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