Diisopropylethylamine → Benzamide

Temperatur

0 °C

2-amino-1-(4-methylpiperidin-1-yl)ethanone represented by Formula 120 (24 mg, 0.15 mmol) was slowly added to 4-benzyloxy-3,4-dimethoxybenzoic acid represented by Formula 89 (48.72 mg, 0.17 mmol) prepared in Preparative Example 1 and diisopropylethylamine (0.11 mL, 0.61 mmol) in DMF (3 mL) at room temperature. After cooling the reaction mixture to 0° C. and adding 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate methanaminium (HATU, 58.41 mg, 0.15 mmol) thereto, the mixture was agitated for 24 hours. The reaction solvent was removed under reduced pressure and chloroform (5 mL) was added to the remaining concentrate to prepare a solution. The solution was washed with a potassium carbonate solution, followed by separation to form an organic layer. After drying the organic layer with sodium sulfate (Na2SO4), the solvent was removed again under reduced pressure and the concentrate mixture was recrystallized using chloroform and hexane, resulting in a benzamide compound represented by Formula 37 as a desired product (VVZ-040; 27.2 mg, 42% yield).

1. customThe reaction solvent was removed under reduced pressure and chloroform (5 mL)
2. additionwas added to the
3. concentrationremaining concentrate
4. customto prepare a solution
5. washThe solution was washed with a potassium carbonate solution
6. customfollowed by separation
7. customto form an organic layer
8. dry with materialAfter drying the organic layer with sodium sulfate (Na2SO4)
9. customthe solvent was removed again under reduced pressure
10. customthe concentrate mixture was recrystallized

ORD-Eintrag

ord-295b678eeac94c98b66e64657784cf79

Quelldatensatz

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09359346B2