Ammonia → HCID 86692091, compound

HRID 570512Notes

Reaction equation

HRID 570512 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=[N:20][NH:21][C:22](=[NH:24])[NH2:23])[CH2:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=1[F:19].N>CN1C(=O)CCC1.[Cu]I>[Cl:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:21]([C:22](=[NH:24])[NH2:23])[N:20]=[C:9]2[CH2:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([F:18])[C:12]=1[F:19]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 178513153HCID 178513153, compound

Product 1

HCID 86692091HCID 86692091, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4.60 g (10.96 mmol) of 2-[1-(2-bromo-5-chlorophenyl)-2-(2,3,6-trifluorophenyl)ethylidene]hydrazinecarboximidamide (the synthesis of this compound is described in WO 2010/065275, Example 3, Step B, page 36-37) and 2.09 g (10.96 mmol) of copper(I) iodide were initially charged in NMP (150 ml) in a 1 l round-bottom flask, and then stirred in an oil bath preheated to 170° C. for 14 minutes. The reaction mixture was subsequently cooled in an ice bath and admixed with an ice/water mixture (400 ml), and concentrated aqueous ammonia solution (200 ml) was added. After stirring for 15 minutes, the solids were filtered off with suction. The residue was dissolved in ethyl acetate, washed twice with water and dried, and the solvent was removed on a rotary evaporator. 3.00 g (39% of theory, 49% purity) of the title compound were obtained. The crude product was reacted further without purification.

Workup

  1. temperatureThe reaction mixture was subsequently cooled in an ice bath
  2. additionwas added
  3. stirringAfter stirring for 15 minutes
  4. filtrationthe solids were filtered off with suction
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed twice with water
  7. customdried
  8. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-dbac730f4dd94dc7a2d9561e8a16842d
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

Loading…