Tetrahydrofuran → Benzamide

As shown in reaction scheme 2 above, after cooling a solution of 5-aminoquinoline represented by Formula 84 (439.93 mg, 3.05 mmol, purchased from TCI Co.) and triethylamine (0.95 mL, 6.78 mmol) in THF (10 mL) at 0° C. under a nitrogen atmosphere, a solution of 4-n-benzyloxy-3,5-dimethoxybenzoic acid chloride represented by Formula 85 (1.04 g, 3.39 mmol) in THF (15 mL) was slowly added to the above cold solution. After agitating the prepared solution at the same temperature for 30 minutes, this solution was left at room temperature for 18 hours. After filtering and removing a precipitate generated during the reaction, the remaining solution was diluted with chloroform and washed with a potassium carbonate solution, followed by separation and drying with (anhydrous) sodium sulfate. A concentrate remaining after removing the solvent under reduced pressure was recrystallized using ethyl acetate and hexane, resulting in a benzamide compound represented by Formula 2 as a desired product (VVZ-001; 1.08 g, 77% yield).

1. customAs shown in reaction scheme 2 above,
2. additionwas slowly added to the above cold solution
3. waitthis solution was left at room temperature for 18 hours
4. filtrationAfter filtering
5. customremoving a precipitate
6. customgenerated during the reaction
7. washwashed with a potassium carbonate solution
8. customfollowed by separation
9. dry with materialdrying with (anhydrous) sodium sulfate
10. customafter removing the solvent under reduced pressure
11. customwas recrystallized

ORD record

ord-7b319b0844f847858b52e40e91d0c9e8

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359346B2