Water → HCID 10003216, compound

HRID 1616523Notes

Reaction equation

HRID 1616523 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:15]1[C:16]([C:22]([NH:24][C:25]2[S:26][CH:27]=[C:28]([CH3:30])[N:29]=2)=[O:23])=[N:17][C:18](Cl)=[CH:19][CH:20]=1.O>CN(C)C=O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[S:1][C:15]1[C:16]([C:22]([NH:24][C:25]2[S:26][CH:27]=[C:28]([CH3:30])[N:29]=2)=[O:23])=[N:17][C:18]([S:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23092625HCID 23092625, compoundHCID 178418616HCID 178418616, compound

Product 1

HCID 10003216HCID 10003216, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Mercaptopyridine (24 mg; 0.205 mmol) and 68 g (0.492 mmol) of potassium carbonate were added to a solution (2 ml) of 3,6-dichloro-N-(4-methyl-thiazole-2-yl)-2-pyridine carboxamide produced by the same method as in Production Example 1 in N,N-dimethylformamide followed by stirring at 100° C. for 15 hours. Water was added to the reaction solution followed by extracting with ethyl acetate and washing with a saturated aqueous saline solution. After drying and concentrating, the resulting residue was purified by a thin-layer silica gel chromatography (chloroform:methanol=20:1) to give 15 mg (yield: 23%) of the title compound as a yellow solid.

Workup

  1. extractionby extracting with ethyl acetate
  2. washwashing with a saturated aqueous saline solution
  3. customAfter drying
  4. concentrationconcentrating
  5. customthe resulting residue was purified by a thin-layer silica gel chromatography (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-ca04ed66622d41aa8972c9b9c476ca9b
Source dataset
uspto-grants-2014_07
Patent number
US08765789B2

Reaction notes

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