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

HRID 2267177Notes

Reaction equation

HRID 2267177 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([C:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH:17]=3)[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)Cl.[C:22]([N:26]=[C:27]=[O:28])([CH3:25])([CH3:24])[CH3:23]>N1C=CC=CC=1>[C:22]([NH:26][C:27]([N:15]1[CH2:14][CH:13]=[C:12]([C:10]2[N:9]=[N:8][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=2)[CH2:17][CH2:16]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 62412tert-Butyl isocyanateHCID 197052864-(1-Phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-[1-Phenyl-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetra-hydropyridine (35 mg) prepared in Example 49 was dissolved in 1 ml of pyridine and 1 ml of chloroform and 26 μl of tert-butyl isocyanate was added thereto followed by stirring at room temperature for 6 hours. The reaction solution was concentrated in vacuo and the resulting residue was separated and purified by a preparative thin-layer chromatography (chloroform/methanol=10/1+0.3% aqueous ammonia) and then recrystallized from chloroform-hexane to give 42 mg of the title compound as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. customthe resulting residue was separated
  3. custompurified by a preparative thin-layer chromatography (chloroform/methanol=10/1+0.3% aqueous ammonia)
  4. customrecrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-1e51854a468f42a395dc199182077bd0
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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