Triethylamine → HCID 59591443, compound

Temperature

0 °C

To an ice cold solution of DMF (0.20 ml) and acetonotrile (5 ml) was added oxalyl chloride (45 μL, 0.52 mmol) dropwise while maintaining the temperature to 0° C. The reaction mixture was stirred at 0° C. for 40 min followed by addition of a solution of 3-((4-bromothiazol-2-yl)methoxy)-2,6-difluorobenzamide (0.15 g, 0.43 mmol) in DMF (2 ml). The resulting reaction mixture was stirred at 0° C. 40 min and then allowed to come to room temperature. After completion of reaction (10 min, TLC monitoring), triethyl amine (100 μL, 0.86 mmol) was added dropwise. The reaction mass was concentrated in vaccuo followed by addition of water (50 ml) and extraction with ethyl acetate (3×75 ml). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (60-120 M, 20% EtOAc-Hexane) to get the desired product (0.10 g, 71%).

1. customThe resulting reaction mixture
2. stirringwas stirred at 0° C
3. custom40 min
4. customto come to room temperature
5. additionwas added dropwise
6. concentrationThe reaction mass was concentrated in vaccuo
7. additionfollowed by addition of water (50 ml) and extraction with ethyl acetate (3×75 ml)
8. washThe combined organics was washed with water, brine
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated
12. customThe crude residue was purified over silica gel (60-120 M, 20% EtOAc-Hexane)

ORD record

ord-4794126c560544f1a5fa4edffbc23c7b

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415383B2