Reaction #674296

Reaction equation

tert-Butyl 6-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)-2-azaspiro[3.3]heptane-2-carboxylate

Toluene

→

(±)-5-(1-(2-azaspiro[3.3]heptan-6-yl)-1H-pyrazol-4-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine formate

Yield 61.0%

Solvents

formic acid

Conditions

Workup

1. 1
   OtherThe solution was sonicated at room temperature for 1.0 h
2. 2
   Concentrationconcentrated by evaporation in vacuo
3. 3
   Otherto give the residue
4. 4
   Otherevaporated again
5. 5
   workup.ADDITIONEther (10 mL) was added
6. 6
   FiltrationThe solid was collected by filtration
7. 7
   Washwashed with ether (10 mL)
8. 8
   Otherdried under high vacuum

Procedure

tert-Butyl 6-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)-2-azaspiro[3.3]heptane-2-carboxylate (53 mg, 0.094 mmol) was dissolved in formic acid (3 mL). The solution was sonicated at room temperature for 1.0 h and then concentrated by evaporation in vacuo to give the residue. Toluene (2×5 mL) was added and evaporated again. Ether (10 mL) was added and the mixture was stirred at room temperature for 1.0 h. The solid was collected by filtration, washed with ether (10 mL) and then dried under high vacuum to afford (±)-5-(1-(2-azaspiro[3.3]heptan-6-yl)-1H-pyrazol-4-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine formate (29 mg, 61%) as an off-white solid.

Source