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

HRID 732152Notes

Reaction equation

HRID 732152 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[O:14][N:13]=[C:12]([NH:15][CH3:16])[N:11]=2)[CH:7]=[CH:8][CH:9]=1.Cl[CH2:18][C:19]1[N:20]([CH3:30])[C:21]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[N:22][N:23]=1.[NH4+].[Cl-]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[O:14][N:13]=[C:12]([N:15]([CH3:16])[CH2:18][C:19]3[N:20]([CH3:30])[C:21]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=4)=[N:22][N:23]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 569243585-(3-chlorophenyl)-N-methyl-1,2,4-oxadiazol-3-amineHCID 589390964-[5-(chloromethyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridine

Product 1

HCID 115018145-(3-chlorophenyl)-N-methyl-N-[(4-methyl-5-pyridin-4-yl-4H-1,2,4-triazol-3-yl) methyl]-1,2,4-oxadiazol-3-amineYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (7.0 mg, 0.35 mmol) was added to a solution of 5-(3-chlorophenyl)-N-methyl-1,2,4-oxadiazol-3-amine (60 mg, 0.29 mmol) in DMF (3 ml) at r.t. After 5 min 4-[5-(chloromethyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridine (60 mg, 0.29 mmol) dissolved in DMF (3 ml) was added. The reaction mixture was stirred for 4 h at r.t. Aq. sat. NH4Cl was added and the mixture was extracted with EA. The organic phase was washed with water and brine, dried and concentrated. Flash chromatography (DCM/MeOH 20:1) afforded 60 mg (54%) of the title compound. 1H NMR: 3.12 (s, 3 H) 3.80 (s, 3 H) 4.94 (s, 2 H) 7.46 (t, 1 H) 7.56 (m, 1 H) 7.58-7.63 (m, 2 H) 7.95 (m, 1 H) 8.06 (t, 1 H) 8.79 (m, 2 H).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with EA
  3. washThe organic phase was washed with water and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6618861b4c7e45c3a88639ba31ffe5a9
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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