Nicotinoyl chloride → 3-(5-(Pyridin-3-yl)-1,2,4-oxadiazol-3-yl)benzonitrile

HRID 450591Notes

Reaction equation

HRID 450591 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6](=[N:8][OH:9])[NH2:7])#[N:2].[C:13](Cl)(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1>N1C=CC=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:13]2[O:9][N:8]=[C:6]([C:5]3[CH:4]=[C:3]([CH:12]=[CH:11][CH:10]=3)[C:1]#[N:2])[N:7]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 573689333-Cyano-N-hydroxy-benzamidine

Product 1

HCID 670261333-(5-(Pyridin-3-yl)-1,2,4-oxadiazol-3-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Cyano-N′-hydroxybenzimidamide (0.322 g, 1 mmol) was dissolved in pyridine (10 mL) and nicotinoyl chloride (Aldrich, 0.141 g, 1 mmol) was added. The reaction mixture was heated to reflux for 3 hours and cooled to room temperature. The cooled reaction mixture was quenched with water (25 mL) and filtered. The solid was further purified with flash column chromatography (5% methanol/dichloromethane) to give the titled compound. 1H NMR (300 MHz, DMSO-d6) δ 7.75-7.71 (dd, J=5.7, 4.1 Hz, 1 H), 7.85 (t, J=7.8 Hz, 1 H), 8.15-8.12 (d, J=7.8 Hz, 1 H) 8.44-8.42 (m, 1 H), 8.50 (m, 1 H), 8.60-8.56 (m, 1 H), 8.93-8.91 (dd, J=1.7 Hz, 1 H), 9.37-9.38 (d, J=1.7 Hz, 1 H) ppm; MS (DCI/NH3) m/z 249 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe cooled reaction mixture
  4. customwas quenched with water (25 mL)
  5. filtrationfiltered
  6. customThe solid was further purified with flash column chromatography (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7144fbbcd0694594be7c91f3252d9812
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

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