Sec-Butylamine → Sec-butyl-[4-(chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridin-2-yl]-amine

HRID 1831551Notes

Reaction equation

HRID 1831551 reaction equation
Cl[CH:2]1[CH:7]([N+:8]([O-:10])=[O:9])[C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[CH:13][C:12]=2[Cl:21])=[CH:5][CH:4]=[N:3]1.[CH:22]([NH2:26])([CH2:24][CH3:25])[CH3:23].CCN(C(C)C)C(C)C>C(#N)C>[CH:22]([NH:26][CH:2]1[CH:7]([N+:8]([O-:10])=[O:9])[C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[CH:13][C:12]=2[Cl:21])=[CH:5][CH:4]=[N:3]1)([CH2:24][CH3:25])[CH3:23]

Participants

5

Reactant 3

HCID 24874Sec-ButylamineHCID 81531DiisopropylethylamineHCID 220520842-Chloro-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridine

Product 1

HCID 22052136Sec-butyl-[4-(chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridin-2-yl]-amineYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-4-(2-chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridine (0.176 g, 0.53 mmol) was dissolved in acetonitrile (20 mL), followed by the addition of sec butylamine (106 μL, 1.06 mmol) and Hunig's base (184 μL, 1.06 mmol). The reaction was stirred at reflux for 64 h. The solution was cooled to room temperature, extracted with EtOAc/H2O, organic layer was then washed with 1N HCl and made basic with 1N NaOH. The organic layer was washed with brine, dried Na2SO4, filtered and concentrated to yield 0.163 g (83%) of sec-butyl-[4-(chloro-4-difluoromethoxy-phenyl)-3-nitro-2,3-dihydro-pyridin-2-yl]-amine as a yellow oil; MS (AP) 413.0 [(M+H+CH3CN)+, 50].

Workup

  1. temperatureat reflux for 64 h
  2. extractionextracted with EtOAc/H2O, organic layer
  3. washwas then washed with 1N HCl
  4. washThe organic layer was washed with brine, dried Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6778c5103ca497e87e38a68657de8ed
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

Loading…