p-Toluenesulfonic acid → HCID 66744217, compound

HRID 2363979Notes

Reaction equation

HRID 2363979 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].[S:16]1(=[O:23])[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[N:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:4][C:3]3[C:13](=[O:14])[NH:15][C:19]4([CH2:20][CH2:21][S:16](=[O:23])[CH2:17][CH2:18]4)[NH:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 544260Tetrahydro-4H-thiopyran-4-one 1-oxideHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 66744217HCID 66744217, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.050 g, 0.23 mmol) in acetic acid (3 mL) were added tetrahydro-4H-thiopyran-4-one 1-oxide (0.061 g, 0.46 mmol) and p-toluenesulfonic acid (0.0040 g, 0.023 mmol). The mixture was heated at 80° C. overnight. Then, the solvent was removed and the obtained residue was taken up in methanol (20 mL). Solid NaHCO3 (1.5 g) was added, and the mixture was stirred for 10 min. The mixture was filtered, and the filtrate was chromatographed (Combiflash, silica gel, dichloromethane to 80:20 dichloromethane/methanol) to give the title compound (0.0127 g, 16%) as a yellow solid:

Workup

  1. customThen, the solvent was removed
  2. additionSolid NaHCO3 (1.5 g) was added
  3. filtrationThe mixture was filtered
  4. customthe filtrate was chromatographed (Combiflash, silica gel, dichloromethane to 80:20 dichloromethane/methanol)

Sources & evidence

ORD record
ord-884c87a727b84258988428ed0ca30223
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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