Ammonium Chloride → HCID 57901835, compound

HRID 1851409Notes

Reaction equation

HRID 1851409 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]#[C:7][C:8]1[C:9]([NH:24]C(=O)C(F)(F)F)=[C:10]([CH:21]=[CH:22][CH:23]=1)[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].[C@@H]1(N)CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.[Cu](I)I>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:24][C:9]2[C:8]([CH:7]=1)=[CH:23][CH:22]=[CH:21][C:10]=2[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 57901577HCID 57901577, compound

Product 1

HCID 57901835HCID 57901835, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution (50 mL) of benzyl 3-(1,3-thiazol-2-ylethynyl)-2-[(trifluoroacetyl)amino]benzoate (2.21 g), copper iodide (0.146 mg), trans-cyclohexane-1,2-diamine (0.177 g) and tripotassium phosphate (3.27 g) in anhydrous 1,4-dioxane was stirred with heating under reflux for 2 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50) to give the title compound (1.20 g, yield 70%) as a pale-yellow oil.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 2 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=10:90-50:50)

Sources & evidence

ORD record
ord-ce31bc3e6d774f08ae78b297707a2f3f
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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