반응 #1706778

반응 방정식

4-{[3-(1-azetidin-3-yl-1H-pyrazol-5-yl)-2′-(trifluoromethyl)biphenyl-4-yl]oxy}-5-chloro-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

formaldehyde

Sodium triacetoxyborohydride

→

solid

수율 132.3%

5-Chloro-2-fluoro-4-({3-[1-(1-methylazetidin-3-yl)-1H-pyrazol-5-yl]-2′-(trifluoromethyl)biphenyl-4-yl}oxy)-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide

수율 132.3%

용매

methanol

dichloromethane

acetic acid

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGwas stirred for 18 hours at room temperature
2. 2
   세척washed with water (3×2 mL)
3. 3
   추출The combined aqueous phases were extracted with dichloromethane (3×5 mL)
4. 4
   건조The combined organic phases were dried over anhydrous sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo

실험 절차

To a suspension of 4-{[3-(1-azetidin-3-yl-1H-pyrazol-5-yl)-2′-(trifluoromethyl)biphenyl-4-yl]oxy}-5-chloro-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 46, 42.9 mg, 0.0659 mmol) in methanol (0.10 mL), dichloromethane (1.72 mL) and acetic acid (0.10 mL) was added formaldehyde (37% w/w, 16.7 μL, 0.224 mmol). The reaction was then stirred under nitrogen at room temperature for 45 minutes. Sodium triacetoxyborohydride (42.6 mg, 0.201 mmol) was added to the reaction which was stirred for 18 hours at room temperature. The reaction was diluted with dichloromethane (20 mL) and washed with water (3×2 mL). The combined aqueous phases were extracted with dichloromethane (3×5 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a white solid (58.0 mg). The solid was purified by B-HPLC to afford the title compound.

출처