Réaction #1495615

Équation de réaction

potassium carbonate

6-Bromospiro[2H-1-benzopyran-3(4H),2′-[1,3]dioxolane]

methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]-methyl]carbamate

trans-N,N′-dimethylcyclohexane-1,2-diamine

→

title compound

Rendement 18.0%

methyl N-[[2-chloro-5-(1-spiro[2H-1-benzopyran-3(4H), 2′-[1,3]dioxolan]-6-yl-1H-pyrazol-3-yl)phenyl]methyl]carbamate

Rendement 18.0%

Solvants

MeOH CHCl3

dioxane

Conditions de réaction

Traitement

1. 1
   Concentrationthe reaction mixture was concentrated under vacuum
2. 2
   AutreThe resultant crude residue was purified on a silica gel column with 1% MeOH/CHCl3 as eluent

Mode opératoire

To a solution of methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]-methyl]carbamate (i.e. the product of Example 8, Step B) (400 mg, 1.50 mmol) in dioxane (16 mL) was added trans-N,N′-dimethylcyclohexane-1,2-diamine (0.30 mmol, 43 mg) under a nitrogen atmosphere. Copper (I) iodide (57 mg, 0.30 mmol) and potassium carbonate (1.24 g, 9.05 mmol) were added to the reaction mixture. 6-Bromospiro[2H-1-benzopyran-3(4H),2′-[1,3]dioxolane] (614 mg, 2.26 mmol) was added last and the reaction mixture was heated at 100° C. under a nitrogen atmosphere overnight. After TLC analysis (10% MeOH/CHCl3) shows 80% conversion of starting material, the reaction mixture was concentrated under vacuum. The resultant crude residue was purified on a silica gel column with 1% MeOH/CHCl3 as eluent to give the title compound, a compound of the present invention, (120 mg, 18% yield) as a solid.

Source