Ammonium Chloride → HCID 59331648, compound

HRID 572217Notes

Reaction equation

HRID 572217 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:12]=[C:13]([NH:17][C:18](=[O:32])[C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([N+:29]([O-])=O)[CH:20]=3)[CH:14]=[CH:15][CH:16]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1.[Cl-].[NH4+].[In]>C(O)C.O>[NH2:29][C:21]1[CH:20]=[C:19]([CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=1)[C:18]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C@@H:9]([NH:8][C:6]2[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[N:7]=2)[CH3:10])[CH:12]=1)=[O:32]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 59331741HCID 59331741, compound

Product 1

HCID 59331648HCID 59331648, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of (S)—N-(3-(1-(6-chloropyrazin-2-ylamino)ethyl)phenyl)-3-nitro-5-(trifluoromethyl)benzamide (74 mg, 0.16 mmol) in ethanol (3 mL) was added a solution of ammonium chloride (85 mg, 1.6 mmol) in water (1.5 mL), then indium powder (73 mg, mesh 100, 0.64 mmol). The mixture was heated at reflux for 40 hours, was allowed to cool to room temperature and was filtered through Celite. The filter cake was washed with ethanol and the combined filtrates were concentrated under reduced pressure. The residue was dissolved in ethyl acetate (30 mL) and water (30 mL), the phases separated and the organic phase washed with brine (30 mL), dried (Na2SO4) and concentrated under reduced pressure to give a yellow oil which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give (S)-3-amino-N-(3-(1-(6-chloropyrazin-2-ylamino)ethyl)phenyl)-5-(trifluoromethyl)benzamide (45 mg, 65%) as a pale yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 40 hours
  3. filtrationwas filtered through Celite
  4. washThe filter cake was washed with ethanol
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  7. customwater (30 mL), the phases separated
  8. washthe organic phase washed with brine (30 mL)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated under reduced pressure
  11. customto give a yellow oil which
  12. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4077f4de96924e0f954fd5a9bb26e59d
Source dataset
uspto-grants-2015_05
Patent number
US09029386B2

Reaction notes

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