Hydroxylamine → 4,5-Dimethyl-3-(5-methyl-[1,2,4]oxadiazol-3-yl-methyl)-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazine

HRID 447135Notes

Reaction equation

HRID 447135 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=3)[CH2:11][CH2:10]2)[N:5]=[N:4][C:3]=1[CH2:25][C:26]#[N:27].O[NH2:29].C1C[O:33][CH2:32][CH2:31]1>COC(OC)(N(C)C)C>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=3)[CH2:13][CH2:14]2)[N:5]=[N:4][C:3]=1[CH2:25][C:26]1[N:29]=[C:32]([CH3:31])[O:33][N:27]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 8028TetrahydrofuranHCID 591914844,5-Dimethyl-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazin-3-yl-acetonitrile

Product 1

HCID 591915674,5-Dimethyl-3-(5-methyl-[1,2,4]oxadiazol-3-yl-methyl)-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazineYield 45%

Reagents, catalysts & solvents 1

HCID 878351,1-Dimethoxyethyl(dimethyl)amineSolvent

Procedure

4,5-Dimethyl-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazin-3-yl-acetonitrile (120 mg, 0.32 mmol) is combined with hydroxyl amine (63 mg, 0.96 mmol) and THF (2 mL). The reaction mixture is heated to reflux for 3 it Concentrate the reaction and redissolve the residue in dimethylacetamide dimethylacetal (500 μL). Heat this solution for 16 h at reflux. Concentrate the resulting mixture in vacuo. The residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2) to afford the title compound (62.3 mg, 45%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 it
  3. concentrationConcentrate
  4. customthe reaction
  5. temperatureHeat this solution for 16 h
  6. temperatureat reflux
  7. concentrationConcentrate the resulting mixture in vacuo
  8. customThe residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-82b5ba3f6e624fc0a9495424895b1e34
Source dataset
uspto-grants-2013_07
Patent number
US08481542B2

Reaction notes

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