p-Toluenesulfonic acid → HCID 66744002, compound

HRID 2363990Notes

Reaction equation

HRID 2363990 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].[F:16][C:17]([F:22])([F:21])[C:18]([CH3:20])=O.CC1C=CC(S(O)(=O)=O)=CC=1.[O-]S([O-])(=O)=O.[Mg+2].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:20][C:18]1([C:17]([F:22])([F:21])[F:16])[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

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 9871Methyl trifluoromethyl ketoneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 66744002HCID 66744002, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (110 mg, 0.502 mmol), 1,1,1-trifluoroacetone (1 mL, 11.2 mmol), PTSA (9.5 mg, 0.050 mmol), MgSO4 (60.4 mg, 0.50 mmol) and DMF (1 mL) was microwave-irradiated at 100° C. for 1 h then at 130° C. for 3 h. Then, the mixture was poured into saturated aqueous NaHCO3 (100 mL). Extraction with EtOAc (100 mL), washing with brine, drying over MgSO4, filtration and concentration under reduced pressure gave a yellow solid. This residue was purified by column chromatography (Purif, NH, hexane to EtOAc) to afford a yellow solid. This solid was triturated with EtOAc/hexane and collected by filtration to afford the title compound (94.3 mg, 60%) as a yellow solid:

Workup

  1. customwas microwave-irradiated at 100° C. for 1 h
  2. extractionExtraction with EtOAc (100 mL)
  3. washwashing with brine
  4. dry with materialdrying over MgSO4, filtration and concentration under reduced pressure
  5. customgave a yellow solid
  6. customThis residue was purified by column chromatography (Purif, NH, hexane to EtOAc)
  7. customto afford a yellow solid
  8. customThis solid was triturated with EtOAc/hexane
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-a1142bef95bb4386904adfd1c3faf4f0
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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