Ethanol → [1-(3-Chloro-benzyl)-1H-[1,2,4]triazol-3-yl]-[1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-yl]-amine

HRID 451406Notes

Reaction equation

HRID 451406 reaction equation
[CH3:1][C:2]1[O:6][C:5]([N:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)=[N:4][N:3]=1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[CH2:18][N:19]1[CH:23]=[N:22][C:21]([NH2:24])=[N:20]1.C(O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1.C(O)(=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[CH2:18][N:19]1[CH:23]=[N:22][C:21]([NH:24][CH:10]2[CH2:11][CH2:12][N:7]([C:5]3[O:6][C:2]([CH3:1])=[N:3][N:4]=3)[CH2:8][CH2:9]2)=[N:20]1

Participants

7

Reactant 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 70193361-(3-chlorobenzyl)-1H-1,2,4-triazol-3-amineHCID 583978531-(5-Methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one

Product 1

HCID 53353333[1-(3-Chloro-benzyl)-1H-[1,2,4]triazol-3-yl]-[1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-yl]-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

A solution of 1-(5-methyl-[1,3,4]oxadiazol-2-yl)-piperidin-4-one (91 mg, 0.5 mmol) and 1-(3-chloro-benzyl)-1H-[1,2,4]triazol-3-ylamine (104 mg, 0.5 mmol) in dry toluene (8 mL) and acetic acid (0.4 mL) was heated under reflux at a Dean-Stark trap for 12 hours. The reaction mixture was cooled to room temperature, ethanol (5 mL) was added, followed by sodium borohydride (19 mg, 0.5 mmol) and stirred at room temperature overnight. The reaction mixture was extracted with water and ethyl acetate, the organic layers were combined, dried over Na2SO4, filtered and the solvents were evaporated. The residue was purified by silica gel chromatography using dichloromethane/methanol as eluent. The title compound was obtained as a white solid (91 mg, 49%).

Workup

  1. temperatureunder reflux at a Dean-Stark trap for 12 hours
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were evaporated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-58feef02b8ec422b98403cc32e527ab4
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

Loading…