Reaktion #493473

Reaktionsgleichung

methyl 5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxylate

trans-3-[(2,3-dichlorophenyl)oxy]cyclobutanamine

triazabicyclodecene

→

title compound

Ausbeute 76.3%

N-{trans-3-[(2,3-Dichlorophenyl)oxy]cyclobutyl}-5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxamide

Ausbeute 76.3%

Lösungsmittel

DCM

THF

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was then transferred to a round bottomed flask
2. 2
   Sonstigeevaporated in vacuo
3. 3
   Sonstigeto give yellow/brown gum which
4. 4
   Sonstigepurified on silica (70 g)
5. 5
   Sonstigeover 40 min
6. 6
   Sonstigeevaporated in vacuo

Vorschrift

A suspension of methyl 5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxylate (438 mg, 1.75 mmol), trans-3-[(2,3-dichlorophenyl)oxy]cyclobutanamine (463 mg, 1.995 mmol) and triazabicyclodecene (75 mg, 0.539 mmol) in THF (0.5 mL) was stirred in a sealed tube at room temperature for 18 hours. The reaction mixture was then transferred to a round bottomed flask using DCM as solvent and evaporated in vacuo to give yellow/brown gum which solidified (1.5 g). This material was dissolved in DCM and purified on silica (70 g) using a 0-100% ethyl acetate-cyclohexane gradient over 40 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound as yellow crystals (601 mg).

Quelle