Dimethylformamide → 2-(4-Chloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetamide

To a mixture of (4-chloro-6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acid (365 mg) and THF (dry) (5 mL) were added oxalyl chloride (0.095 mL) and DMF (6.98 μl) at room temperature. The mixture was stirred at room temperature for 20 min. The mixture was concentrated under reduced pressure. The residue was dissolved in THF (5 mL), and the solution was poured into stirred 28% aqueous ammonium hydroxide (5 mL) at room temperature. After stirring at room temperature for 15 min, the mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The solid was crystallized from MeOH to give the title compound (320 mg).

1. concentrationThe mixture was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in THF (5 mL)
3. additionthe solution was poured
4. stirringinto stirred 28% aqueous ammonium hydroxide (5 mL) at room temperature
5. stirringAfter stirring at room temperature for 15 min
6. additionthe mixture was poured into water at room temperature
7. extractionextracted with EtOAc
8. customThe organic layer was separated
9. washwashed with brine
10. dry with materialdried over MgSO4
11. concentrationconcentrated in vacuo
12. customThe solid was crystallized from MeOH

ORD 기록

ord-a39c563ee48e43b3ac9292b84feaf863

출처 데이터셋

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09238639B2