Methyl iodide → methyl 1,4-dihydro-3-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-1,2,6-trimethyl-4-(3-nitrophenyl)pyridine-5-carboxylate

HRID 247126Notes

Reaction equation

HRID 247126 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:36])=[C:5]([C:32]([O:34][CH3:35])=[O:33])[CH:6]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:7]=1[C:8]1[O:12][N:11]=[C:10]([CH2:13][N:14]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:15])[N:9]=1.[H-].[Na+].[CH3:39]I>CN(C=O)C>[CH2:16]([N:14]([CH2:13][C:10]1[N:9]=[C:8]([C:7]2[CH:6]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)[C:5]([C:32]([O:34][CH3:35])=[O:33])=[C:4]([CH3:36])[N:3]([CH3:39])[C:2]=2[CH3:1])[O:12][N:11]=1)[CH3:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128443SM 6586

Product 1

HCID 20161255methyl 1,4-dihydro-3-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-1,2,6-trimethyl-4-(3-nitrophenyl)pyridine-5-carboxylateYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 250 mg of methyl 1,4-dihydro-2,6-dimetyl-3-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-4-(3-nitrophenyl)pyridine-5-carboxylate in 5 ml of dry DMF was added 24 mg of 60% sodium hydride with ice-cooling. After the mixture was stirred for 10 minutes, there was added 76 mg of methyl iodide. The reaction mixture was allowed to stand at room temperature for 6 hours, diluted by addition of ice-water and then extracted with ethyl acetate. The extracts were washed with water, dried and evaporated in vacuo. The residue was chromatographed on silica gel using chloroform-methanol (30:1) as eluent to give 190 mg of methyl 1,4-dihydro-3-[3-(N-benzyl-N-methylamino)methyl-1,2,4-oxadiazol-5-yl]-1,2,6-trimethyl-4-(3-nitrophenyl)pyridine-5-carboxylate, IR νmaxneat cm-1 : 1690, 1635, 1580, 1520, 1340, 900.

Workup

  1. temperaturecooling
  2. waitto stand at room temperature for 6 hours
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-7c0fa431e9ed41a7bd5ee0db23343137
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

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