1,2-Dichloroethane → HCID 178506230, compound

HRID 491610Notes

Reaction equation

HRID 491610 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:9]=[C:10]([NH2:15])[C:11]([NH2:14])=[CH:12][CH:13]=2)=[CH:3][CH:2]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=S)=[CH:19][C:18]=1[C:26]([F:29])([F:28])[F:27].C(Cl)CCl>CC#N>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[NH:14][C:11]3[CH:12]=[CH:13][C:8]([O:7][C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)=[CH:9][C:10]=3[N:15]=2)=[CH:19][C:18]=1[C:26]([F:27])([F:28])[F:29]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5200261-Chloro-4-isothiocyanato-2-(trifluoromethyl)benzeneHCID 177558374-(3,4-Diamino-phenoxy)-pyridine

Product 1

HCID 178506230HCID 178506230, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4-(pyridin-4-yloxy)-benzene-1,2-diamine (0.273 g, 1.36 mmol) in 20 mL CH3CN was added 1-chloro-4-isothiocyanato-2-trifluoromethyl-benzene (prepared similarly to the procedure described in Preparation III, 0.322 g, 1.36 mmol). The reaction was stirred 18 h at RT. The reaction was diluted with 25 mL CH3CN, and then EDC (0.39 g, 2.03 mmol) was added. The reaction was heated at 80° C. for 2.5 h. The reaction was cooled to RT and concentrated in vacuo. The crude mix was dissolved into 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. The partially pure compound was triturated with CH2Cl2 to yield the title compound. MS (MH+)=405.1; Calc'd 404.78 for C19H12ClF3N4O.

Workup

  1. customprepared similarly to the procedure
  2. temperatureThe reaction was heated at 80° C. for 2.5 h
  3. temperatureThe reaction was cooled to RT
  4. concentrationconcentrated in vacuo
  5. additionThe crude mix
  6. dissolutionwas dissolved into EtOAc and water
  7. customThe layers were separated
  8. washthe organic layer was washed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by silica gel column chromatography
  13. customThe partially pure compound was triturated with CH2Cl2

Sources & evidence

ORD record
ord-611cfb898ac04e53a7044f376098c343
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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