Sodium hydride → 3-(3-{[[5-(2-methoxypyridin-4-yl)-4-methyl-4H-1,2,4-triazol-3-yl](methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)benzonitrile

HRID 732147Notes

Reaction equation

HRID 732147 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([C:11]2[N:12]([CH3:18])[C:13]([NH:16][CH3:17])=[N:14][N:15]=2)[CH:8]=[CH:7][N:6]=1.CS(O[CH2:24][C:25]1[N:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]#[N:37])[CH:31]=2)[O:27][N:26]=1)(=O)=O>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([C:11]2[N:12]([CH3:18])[C:13]([N:16]([CH2:24][C:25]3[N:29]=[C:28]([C:30]4[CH:31]=[C:32]([CH:33]=[CH:34][CH:35]=4)[C:36]#[N:37])[O:27][N:26]=3)[CH3:17])=[N:14][N:15]=2)[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 57837975[5-(3-Cyanophenyl)-1,2,4-oxadiazol-3-yl]methyl methanesulfonateHCID 578379845-(2-methoxypyridin-4-yl)-N,4-dimethyl-4H-1,2,4-triazol-3-amine

Product 1

HCID 115169363-(3-{[[5-(2-methoxypyridin-4-yl)-4-methyl-4H-1,2,4-triazol-3-yl](methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)benzonitrileYield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.013 g, 0.53 mmol) was added portionwise to a stirred solution of 5-(2-methoxypyridin-4-yl)-N,4-dimethyl-4H-1,2,4-triazol-3-amine (0.086 g; 0.39 mmol) in DMF (10 ml) at 0° C. The mixture was stirred for 30 minutes before [5-(3-cyanophenyl)-1,2,4-oxadiazol-3-yl]methyl methanesulfonate (0.1 g; 0.36 mmol) in DMF (1 ml) was added dropwise. The mixture was stirred at r.t. for 3 h before quenching with water (30 ml). The resulting mixture was extracted with EA (3×40 ml). The organics were combined, dried (Na2SO4) and evaporated to give a crude material, which was purified by prep. HPLC to give the title compound (0.061 g; 42.3%). 1H NMR: 8.49 (s, 1H), 8.33 (dd, 1H), 8.28 (d, 1H), 7.86 (dd, 1H), 7.67 (t, 1H), 7.24 (d, 1H), 7.02 (s, 1H), 4.60 (s, 2H), 3.97 (s, 3H), 3.70 (s, 3H), 3.08 (s, 3H).

Workup

  1. additionwas added dropwise
  2. custombefore quenching with water (30 ml)
  3. extractionThe resulting mixture was extracted with EA (3×40 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a crude material, which
  7. customwas purified by prep

Sources & evidence

ORD record
ord-d02408bcd40841299a23636c0c18acf2
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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