Sodium hydride → N-{1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl}-N,4-dimethyl-5-pyridin-3-yl-4H-1,2,4-triazol-3-amine

HRID 732142Notes

Reaction equation

HRID 732142 reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5]1[N:9]([CH3:10])[C:8]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:7][N:6]=1.Cl[CH:18]([C:20]1[N:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[O:22][N:21]=1)[CH3:19]>CN(C=O)C.[Cl-].[Na+].O>[Cl:31][C:27]1[CH:26]=[C:25]([C:23]2[O:22][N:21]=[C:20]([CH:18]([N:4]([CH3:3])[C:5]3[N:9]([CH3:10])[C:8]([C:11]4[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=4)=[N:7][N:6]=3)[CH3:19])[N:24]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 57837974N,4-dimethyl-5-pyridin-3-yl-4H-1,2,4-triazol-3-amineHCID 578379793-(1-Chloroethyl)-5-(3-chlorophenyl)-[1,2,4]oxadiazole

Product 1

HCID 11661206N-{1-[5-(3-chlorophenyl)-1,2,4-oxadiazol-3-yl]ethyl}-N,4-dimethyl-5-pyridin-3-yl-4H-1,2,4-triazol-3-amineYield 43.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
60 °C

Procedure

NaH (14 mg, 0.35 mmol) was added to N,4-dimethyl-5-pyridin-3-yl-4H-1,2,4-triazol-3-amine (33 mg, 0.18 mmol) in DMF (3 mL). After 30 min 3-(1-chloroethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole (80 mg, 0.18 mmol) in DMF (1 mL) was added to the mixture and the reaction was stirred at 60° C. o.n. Brine was added and the mixture was extracted with EA. The organic phase was dried and concentrated. The product was purified by column chromatography (DCM to DCM-MeOH 30:1) to give 31 mg (43%) of the title compound. 1H NMR: 1.71 (d, 3H) 2.97 (s, 3H) 3.67 (s, 3H) 4.88 (q, 1H) 7.46 (m, 2H) 7.56 (d, 1H) 8.00 (d, 1H) 8.10 (d, 2H) 8.71 (bs, 1H) 8.92 (bs, 1H)

Workup

  1. extractionthe mixture was extracted with EA
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customThe product was purified by column chromatography (DCM to DCM-MeOH 30:1)

Sources & evidence

ORD record
ord-da0e5fdc7cac4df7856ca6db9f84d3c2
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

Loading…