Reaktion #68101

Reaktionsgleichung

1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxylic acid

1,1′-carbonyldiimidazole

methanesulfonamide

1,8-diazabicylo[5.4.0] undec-7-ene

→

tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-(((methylsulfonyl)amino)carbonyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Ausbeute 88.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturThe reaction mixture was cooled to the room temperature
3. 3
   workup.STIRRINGstirred at room temperature for 2 hours
4. 4
   SonstigeThe solvent was removed under reduced pressure, water
5. 5
   workup.ADDITIONwas added
6. 6
   FiltrationThe resulting solid was filtered

Vorschrift

To 5 mL of tetrahydrofuran suspension containing 0.10 g of 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxylic acid, 58 mg of 1,1′-carbonyldiimidazole was added, and stirred at 50° C. for 1 hour. The reaction mixture was cooled to the room temperature, then 84 mg of methanesulfonamide and 0.13 mL of 1,8-diazabicylo[5.4.0] undec-7-ene were added, and stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, water was added, and adjusted to pH 4 with 1 mol/L hydrochloric acid. The resulting solid was filtered to afford 0.10 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-(((methylsulfonyl)amino)carbonyl)-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a white solid.

Quelle