Tetrahydrofuran → 4-[1-Phenyl-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetra-hydropyridine-1-carboxylic acid methyl tert-butylamide

HRID 2267180Notes

Reaction equation

HRID 2267180 reaction equation
[C:1]([NH:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:15]=[N:16][N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[K+].O1CCC[CH2:28]1>>[CH3:28][N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[N:15]=[N:16][N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:18]=2)[CH2:12][CH2:13]1)=[O:7]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 82127Potassium hydrideHCID 589458634-[1-Phenyl-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetra-hydropyridine-1-carboxylic acid tert-butylamide

Product 1

HCID 589458144-[1-Phenyl-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetra-hydropyridine-1-carboxylic acid methyl tert-butylamide

Procedure

4-[1-Phenyl-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetra-hydropyridine-1-carboxylic acid tert-butylamide (15 mg) prepared in Example 74 was added to a solution of 35 mg of potassium hydride in 1 ml of tetrahydrofuran washed with hexane. After stirring at room temperature for 10 minutes, 20 μl of methyl iodide was added thereto and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction solution followed by extracting with chloroform. The resulting organic layer washed with a saturated aqueous solution of sodium bicarbonate and then with a saturated saline solution, dried over sodium sulfate and the solvent was evaporated in vacuo. The resulting residue was separated and purified by a preparative thin-layer chromatography (chloroform/methanol=20/1+0.3% aqueous ammonia) to give 8.5 mg of the title compound as a white solid

Workup

  1. washwashed with hexane
  2. addition20 μl of methyl iodide was added
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. additionWater was added to the reaction solution
  5. extractionby extracting with chloroform
  6. washThe resulting organic layer washed with a saturated aqueous solution of sodium bicarbonate
  7. dry with materialwith a saturated saline solution, dried over sodium sulfate
  8. customthe solvent was evaporated in vacuo
  9. customThe resulting residue was separated
  10. custompurified by a preparative thin-layer chromatography (chloroform/methanol=20/1+0.3% aqueous ammonia)

Sources & evidence

ORD record
ord-c19a1d50a3bd469c8d5b9cc393e56fb2
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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