Réaction #1495612

Équation de réaction

K2CO3

Methyl 6-bromo-2H-1-benzopyran-3-carboxylate

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

product

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

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

→

methyl 6-[3-[4-chloro-3-[[(methoxycarbonyl)amino]-methyl]phenyl]-1H-pyrazol-1-yl]-2H-1-benzopyran-3-carboxylate

Rendement 16.0%

Solvants

MeOH CHCl3

dioxane

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture was cooled
2. 2
   Concentrationconcentrated under vacuum
3. 3
   AutreThe crude residue was purified on a silica gel column with 1% MeOH/CHCl3 as eluent
4. 4
   Autreto give compound number 23

Mode opératoire

To a solution of methyl N-[[2-chloro-5-(1H-pyrazol-3-yl)phenyl]-methyl]carbamate (i.e. the product of 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 K2CO3 (1.24 g, 9.05 mmol) were added to the reaction mixture. Methyl 6-bromo-2H-1-benzopyran-3-carboxylate (607 mg, 2.26 mmol) was added to the reaction mixture last. The reaction mixture was heated at 100° C. under a nitrogen atmosphere overnight. After TLC analysis (10% MeOH/CHCl3) showed 80% conversion of the starting material, the reaction mixture was cooled and concentrated under vacuum. The crude residue was purified on a silica gel column with 1% MeOH/CHCl3 as eluent to give compound number 23, a compound of the present invention, (110 mg, 16% yield) as solid.

Source