반응 #165806

반응 방정식

TFA

tert-butyl N-[[3-[5-[3-amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]carbamate

bicarbonate

→

product

수율 92.1%

4-[5-amino-6-[5-[3-(aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide

수율 92.1%

용매

dichloromethane

methanol

dichloromethane

반응 조건

후처리

1. 1
   기타was flushed further with methanol (5 mL)
2. 2
   농축The filtrate was concentrated in vacuo
3. 3
   기타to leave a yellow/orange solid
4. 4
   세척The cartridge was washed initially with methanol
5. 5
   세척the product eluted with 2M ammonia in methanol solution over 4 fractions
6. 6
   기타A yellow solid crystallised out of the filtrate which
7. 7
   기타was isolated by filtration

실험 절차

TFA (131.1 mg, 88.58 μL, 1.150 mmol) was added to a solution of tert-butyl N-[[3-[5-[3-amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]carbamate (60 mg, 0.1150 mmol) in dichloromethane (2 mL) and the resulting solution stirred at room temperature overnight. The reaction mixture was passed through a bicarbonate cartridge, which was flushed further with methanol (5 mL). The filtrate was concentrated in vacuo to leave a yellow/orange solid. The solid was taken up in a mixture of methanol and dichloromethane and passed through an SCX cartridge. The cartridge was washed initially with methanol and then the product eluted with 2M ammonia in methanol solution over 4 fractions. A yellow solid crystallised out of the filtrate which was isolated by filtration to give the product (44 mg, 90% yield) 1H NMR (400 MHz, DMSO) d 2.98 (m, 6H), 3.87 (s, 2H), 7.55 (m, 2H), 7.59-7.66 (m, 2H), 7.81 (br s, 2H), 8.00 (m, 1H), 8.17 (m, 3H) and 8.99 (s, 1H) ppm; MS (ES+) 416.26

출처