4-Heptanone → HCID 66743793, compound

HRID 2363968Notes

Reaction equation

HRID 2363968 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][CH2:18][C:19](=O)[CH2:20][CH2:21][CH3:22].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][CH2:21][CH3:22])[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)[CH2:17][CH3:16]

Participants

6

Reactant 4

HCID 312464-HeptanoneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 66743793HCID 66743793, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.120 g, 0.550 mmol), 4-heptanone (1.0 mL), p-toluenesulfonic acid monohydrate (0.0095 g, 0.050 mmol) and acetic acid (1.5 mL) was stirred for 1 h at 100° C. in a sealed tube. Then, this mixture was stirred for 2 h at 120° C. and stirring was continued for 2 h at 110° C. The mixture was poured into sat. aqueous sodium hydrogen carbonate (150 mL). Extraction with ethyl acetate, drying over magnesium sulfate, filtration and concentration at reduced pressure gave a solid. This solid was triturated with dichloromethane (10 mL), and the precipitate was collected by filtration. Then, the obtained solid was stirred at 60° C. in ethyl acetate (5 mL). After 10 min, the mixture was cooled, and the precipitate was collected by filtration to afford the title compound (0.0406 g, 23%) as a yellow solid:

Workup

  1. stirringThen, this mixture was stirred for 2 h at 120° C.
  2. stirringstirring
  3. waitwas continued for 2 h at 110° C
  4. extractionExtraction with ethyl acetate
  5. dry with materialdrying over magnesium sulfate, filtration and concentration at reduced pressure
  6. customgave a solid
  7. customThis solid was triturated with dichloromethane (10 mL)
  8. filtrationthe precipitate was collected by filtration
  9. stirringThen, the obtained solid was stirred at 60° C. in ethyl acetate (5 mL)
  10. waitAfter 10 min
  11. temperaturethe mixture was cooled
  12. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-1b376ccb15ec4c8dac4ea7e4d912770e
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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