반응 #166756

반응 방정식

N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)butyramide

DIEA

HOBT H2O

EDCI

Na2CO3

(S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid

→

(S)-tert-butyl 3-(4-(3-butyramido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate

수율 47.0%

용매

DCM

반응 조건

후처리

1. 1
   추출extracted into DCM
2. 2
   기타dried
3. 3
   여과filtered
4. 4
   농축concentrated
5. 5
   기타to give a crude residue that
6. 6
   기타was purified by column chromatography (500:10-500:20 DCM:MeOH)

실험 절차

N-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)butyramide (0.050 g, 0.174 mmol), (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (0.0625 g, 0.183 mmol, see Example H), HOBT-H2O (0.0373 g, 0.244 mmol), and EDCI (0.0434 g, 0.226 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.152 mL, 0.870 mmol) was then added, and the reaction was stirred at room temperature for 5 hours. The reaction was then poured into saturated Na2CO3 and extracted into DCM. The organic fractions were combined, dried, filtered and concentrated to give a crude residue that was purified by column chromatography (500:10-500:20 DCM:MeOH) to give (S)-tert-butyl 3-(4-(3-butyramido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate (0.050 g, 47.0% yield).

출처