Ammonium Chloride → HCID 44185965, compound

HRID 1864668Notes

Reaction equation

HRID 1864668 reaction equation
[Cl-].[NH4+].[NH2:3][C:4]1[C:9]([N+:10]([O-])=O)=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([F:34])([F:33])[F:32])[CH:25]=3)=[O:22])=[C:16]([S:35][CH3:36])[CH:15]=2)[CH:7]=[CH:6][N:5]=1>C(O)C.O.[Fe]>[NH2:3][C:4]1[C:9]([NH2:10])=[C:8]([O:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([F:34])([F:32])[F:33])[CH:25]=3)=[O:22])=[C:16]([S:35][CH3:36])[CH:15]=2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 44185903HCID 44185903, compound

Product 1

HCID 44185965HCID 44185965, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of iron powder (4 equivalents, 78 mg, 1.4 mmol) and ammonium chloride (5.8 equivalents, 109 mg, 2 mmol) in ethanol (400 μL) and water (438 μL) was heated to reflux. 1-(4-(2-amino-3-nitropyridin-4-yl-oxy)-2-(methylthio)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea (180 mg, 0.35 mmol) was added in portions and the mixture stirred at reflux for 24 hours. After cooling to room temperature, the slurry mixture was filtered and washed with ethanol. After removal of the solvent, the crude powder was dissolved into EtOAc, filtered to removed the precipitate, and evaporated to provide the title compound (100 mg, 59%) as a sticky dark oil. 1H-NMR (δ, ppm, DMSO-d6): 2.41 (s, 3H, CH3), 5.61 (s, 2H, NH2,Py), 6.06 (d, 1H, HPy,5, J=5.6 Hz), 6.79 (d, 1H, Harom, J=8.7 Hz), 7.01 (s, 1H, Harom), 7.26 (d, 1H, HPy,6, J=5.6 Hz), 7.58-7.69 (m, 4H, Harom), 8.12 (s, 2H, NH2,Py), 8.27 (s, 1H, NHurea1), 10.02 (s, 1H, NHurea3). LC-MS (m/z): 484 (M+H, 100).

Workup

  1. temperaturewas heated to reflux
  2. temperatureat reflux for 24 hours
  3. filtrationthe slurry mixture was filtered
  4. washwashed with ethanol
  5. customAfter removal of the solvent
  6. dissolutionthe crude powder was dissolved into EtOAc
  7. filtrationfiltered
  8. customto removed the precipitate
  9. customevaporated

Sources & evidence

ORD record
ord-972911b054874daaa0897b7417f8d64c
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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