Reaktion #68548

Reaktionsgleichung

(S)-tert-Butyl 3-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamido)pyrrolidine-1-carboxylate

hydrochloric acid

potassium carbonate

→

(S)-3-((7-methoxyquinolin-4-yloxy)methyl)-N-(pyrrolidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide

Ausbeute 97.1%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthen concentrated under vacuum
2. 2
   workup.DISSOLUTIONThe remaining solid was dissolved in methanol (1 mL)
3. 3
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 1 hour
4. 4
   Einengenconcentrated under vacuum
5. 5
   SonstigeThe sample was purified by flash chromatography
6. 6
   Wascheneluting with 10%-15% 7N ammonia in methanol/dichloromethane

Vorschrift

(S)-tert-Butyl 3-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamido)pyrrolidine-1-carboxylate (0.050 g, 0.096 mmol) was dissolved in methanol (1.5 mL) then added concentrated hydrochloric acid (0.400 ml, 4.8 mmol). The reaction mixture was stirred at room temperature for 5 hours then concentrated under vacuum. The remaining solid was dissolved in methanol (1 mL) then added potassium carbonate (0.062 g, 0.45 mmol). The reaction mixture was stirred at room temperature for 1 hour and concentrated under vacuum. The sample was purified by flash chromatography eluting with 10%-15% 7N ammonia in methanol/dichloromethane to afford (S)-3-((7-methoxyquinolin-4-yloxy)methyl)-N-(pyrrolidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridine-6-carboxamide (0.039 g, 97% yield) as a pale yellow solid.

Quelle