Hydrochloric Acid → HCID 68293128, compound

HRID 68569Notes

Reaction equation

HRID 68569 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:25])([F:24])[F:23])[O:13][N:12]=[C:11]([C:14]3[S:18][C:17]([CH3:19])=[C:16]([C:20]#[N:21])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:23])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[S:18][C:17]([CH3:19])=[C:16]([CH2:20][NH2:21])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68279980HCID 68279980, compound

Product 1

HCID 68293128HCID 68293128, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane dimethyl sulfide complex (0.73 ml) is added to a solution of 5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-thiophene-3-carbonitrile (2.8 g) in THF (21 ml) at reflux. After 30 minutes at reflux, the reaction is cooled down to room temperature. HCl (6.2 ml, 1.25M in MeOH) is added and the reaction mixture is refluxed for 30 minutes. The mixture is then concentrated in vacuo to yield C-{5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-thiophen-3-yl}-methylamine as a brown foam (2.9 g). The crude product is used without further purification.

Workup

  1. temperatureat reflux
  2. temperatureAfter 30 minutes at reflux
  3. temperaturethe reaction mixture is refluxed for 30 minutes
  4. concentrationThe mixture is then concentrated in vacuo

Sources & evidence

ORD record
ord-f6483cf16d2540649d0aed0d0451d666
Source dataset
uspto-grants-2014_09
Patent number
US08822466B2

Reaction notes

Loading…