반응 #1706779

반응 방정식

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

formaldehyde

Sodium triacetoxyborohydride

→

gum

수율 122.7%

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

수율 122.7%

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 layers 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)-4′-(trifluoromethyl)biphenyl-4-yl]oxy}-5-chloro-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 41, 46.3 mg, 0.0711 mmol) in methanol (0.11 mL), dichloromethane (1.86 mL) and acetic acid (0.11 mL) was added formaldehyde (37% w/w, 19.6 μL, 0.263 mmol). The reaction was then stirred under nitrogen at room temperature for 45 minutes. Sodium triacetoxyborohydride (45.9 mg, 0.217 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 layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a clear gum (58.0 mg). The clear gum was purified by B-HPLC to afford the title compound.

출처