Cesium carbonate → 3-{[4-(2-methoxyethoxy)phenyl]thio}-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide

HRID 2196605Notes

Reaction equation

HRID 2196605 reaction equation
Br[CH2:2][CH2:3][O:4][CH3:5].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:20]2[C:21]([C:33]([NH:35][C:36]3[S:40][N:39]=[C:38]([CH3:41])[N:37]=3)=[O:34])=[N:22][C:23]([S:26][C:27]3[N:31]([CH3:32])[CH:30]=[N:29][N:28]=3)=[CH:24][CH:25]=2)=[CH:15][CH:14]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:5][O:4][CH2:3][CH2:2][O:12][C:13]1[CH:14]=[CH:15][C:16]([S:19][C:20]2[C:21]([C:33]([NH:35][C:36]3[S:40][N:39]=[C:38]([CH3:41])[N:37]=3)=[O:34])=[N:22][C:23]([S:26][C:27]3[N:31]([CH3:32])[CH:30]=[N:29][N:28]=3)=[CH:24][CH:25]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 809722-Bromoethyl methyl etherHCID 597062523-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide

Product 1

HCID 597062533-{[4-(2-methoxyethoxy)phenyl]thio}-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

0.43 ml of 1-bromo-2-methoxyethane and 4.99 g of cesium carbonate were added to a dimethylformamide (20 ml) solution of 2 g of 3-[(4-hydroxyphenyl)thio]-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide obtained in Reference Example (step 3), and stirred at 60° C. for 1 hour. At room temperature, aqueous saturated ammonium chloride solution was added to it, extracted with chloroform, and the organic layer was washed with saturated saline water. This was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol) and crystallized from ethanol to obtain 1.43 g of the entitled compound as a yellow solid.

Workup

  1. extractionextracted with chloroform
  2. washthe organic layer was washed with saturated saline water
  3. dry with materialThis was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol)
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-627973c679e6412c8e7865dfa184c317
Source dataset
uspto-grants-2012_12
Patent number
US08338460B2

Reaction notes

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