Tetrahydrothiopyran-4-one → HCID 66743289, compound

HRID 2363974Notes

Reaction equation

HRID 2363974 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[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>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][CH2:17][CH2:18]4)[NH:1][C:2]=3[CH:6]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 66173Tetrahydrothiopyran-4-oneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 99208523-Amino-5-(pyridin-4-yl)thiophene-2-carboxamide

Product 1

HCID 66743289HCID 66743289, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-amino-5-(pyridin-4-yl)thiophene-2-carboxamide (0.200 g, 0.910 mmol) and tetrahydrothiopyran-4-one (0.528 g, 4.55 mmol) in glacial acetic acid (6 mL) was added p-toluenesulfonic acid monohydrate (0.017 g, 0.091 mmol). The mixture was heated at 80° C. overnight. Then, the mixture was concentrated, and then the residue was dissolved in methanol (20 mL). Solid NaHCO3 (1.00 g, 11.9 mmol) was added, and the mixture was stirred briefly. The solvent was then removed, and the obtained residue was chromatographed (Combiflash, silica gel, dichloromethane to 93:7 dichloromethane/methanol) to give the title compound (0.263 g, 91%) as a yellow solid:

Workup

  1. concentrationThen, the mixture was concentrated
  2. dissolutionthe residue was dissolved in methanol (20 mL)
  3. customThe solvent was then removed
  4. customthe obtained residue was chromatographed (Combiflash, silica gel, dichloromethane to 93:7 dichloromethane/methanol)

Sources & evidence

ORD record
ord-5e93e0c9cb2743c3b34dcf2962ed7503
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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