Ammonia → HCID 9900262, compound

HRID 431950Notes

Reaction equation

HRID 431950 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[C:14]([CH2:20]Br)[CH:13]=2)[O:9][N:8]=1.[NH3:22]>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[C:14]([CH2:20][NH2:22])[CH:13]=2)[O:9][N:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 219425773-(2-Pyridyl)-5-(3-bromomethyl-5-cyanophenyl)-1,2,4-oxadiazole

Product 1

HCID 9900262HCID 9900262, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 3-(2-pyridyl)-5-(3-bromomethyl-5-cyanophenyl)-1,2,4-oxadiazole (0.5 g, 1.91 mmol) in dichloromethane (1.5 mL) was treated with a 0.5M ammonia (1.5 mL, 1.5 mmol, dioxane) and heated at 50° C. for 90 minutes. After this time the reaction mixture was cooled and diluted with dichloromethane. The organic solution was washed with water and brine. Silica gel chromatography of the crude product afforded 3.5 mg (5.5%) of 3-(2-pyridyl)-5-(3-aminomethyl-5-cyanophenyl)-1,2,4-oxadiazole.

Workup

  1. temperatureAfter this time the reaction mixture was cooled
  2. washThe organic solution was washed with water and brine

Sources & evidence

ORD record
ord-930e2af158c54454a92de64302733103
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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