Sodium hydride → [5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-methyl-(4-methyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-amine

HRID 273167Notes

Reaction equation

HRID 273167 reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5]1[N:9]([CH3:10])[C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:7][N:6]=1.Cl[CH2:18][C:19]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[O:21][N:20]=1>CN(C=O)C>[Cl:30][C:26]1[CH:25]=[C:24]([C:22]2[O:21][N:20]=[C:19]([CH2:18][N:4]([CH3:3])[C:5]3[N:9]([CH3:10])[C:8]([C:11]4[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=4)=[N:7][N:6]=3)[N:23]=2)[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 100825203-(Chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazoleHCID 57837980Methyl-(4-methyl-5-pyridin-4-yl4H-[1,2,4]triazol-3-yl)-amine

Product 1

HCID 67070962[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-methyl-(4-methyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-amineYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

10 mg (0.4 mmol) NaH was added to a solution of 38 mg (0.2 mmol) methyl-(4-methyl-5-pyridin-4-yl-4H-[1,2,4]triazol-3-yl)-amine in 3 ml DMF under an atmosphere of nitrogen. After 10 min a solution of 50 mg (0.22 mmol) 3-chloromethyl-5-(3-chloro-phenyl)-[1,2,4]oxadiazole in 2 ml DMF was added. After stirring for 45 min NH4Cl(sat) was added and the mixture was extracted twice with CHCl3. The organic phase was dried and concentrated. Flashchromatography (CH2Cl2/MeOH 20:1) afforded 41 mg (54%) of the desired product. 1H NMR (CDCl3), d (ppm): 3.07 (s, 3 H) 3.71 (s, 3 H) 4.56 (s, 2 H) 7.45 (m, 1 H) 7.55 (m, 1 H) 7.62 (d, 2 H) 7.98 (d, 1 H) 8.09 (m, 1 H) 8.73 (d, 2 H).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted twice with CHCl3
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f1a2d50f27e94b27942ad5d290cc9bd3
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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