1,2-Dichloroethane → HCID 178485501, compound

HRID 491613Notes

Reaction equation

HRID 491613 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH2:19])[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=S)=[CH:23][C:22]=1[C:30]([F:33])([F:32])[F:31].C(Cl)CCl>CC#N>[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]3[NH:18][C:28]([NH:27][C:24]4[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:30]([F:33])([F:31])[F:32])[CH:23]=4)=[N:19][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5200261-Chloro-4-isothiocyanato-2-(trifluoromethyl)benzeneHCID 177564924-(3,4-Diamino-phenoxy)-pyridine-2-carboxylic acid methylamide

Product 1

HCID 178485501HCID 178485501, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

To a solution of 4-(3,4-diamino-phenoxy)-pyridine-2-carboxylic acid methylamide (Step B) (0.07 g, 0.27 mmol) in 20 mL CH3CN was added dropwise, over 5 min, a solution 1-chloro-4-isothiocyanato-2-trifluoromethyl-benzene (0.055 g, 0.27 mmol) in 10 mL CH3CN. The reaction was stirred 18 h at RT. The reaction was diluted with 10 mL CH3CN, then EDC (0.078 g, 0.41 mmol) was added. The reaction was heated at 80° C. for 3 h. The reaction was cooled to RT and concentrated in vacuo. The crude mix was dissolved in EtOAc and water. The layers were separated, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a hexane-EtOAc gradient to yield the title compound. MS (MH+)=461.9; MW Calc'd 461.09 for C21H15ClF3N5O2.

Workup

  1. temperatureThe reaction was heated at 80° C. for 3 h
  2. temperatureThe reaction was cooled to RT
  3. concentrationconcentrated in vacuo
  4. additionThe crude mix
  5. dissolutionwas dissolved in EtOAc
  6. customThe layers were separated
  7. washthe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-390f6d182b5b4dfeb747962d784f5010
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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