1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 131731885, compound

5-(3-Methoxyphenyl)-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyri dine (0.045 g, 0.118 mmol, see Example 8) and (S)-3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (0.0424 g, 0.124 mmol, see Example H) were placed in DCM (3 mL). HOBT-H2O (0.0253 g, 0.165 mmol), EDCI (0.0294 g, 0.153 mmol), and DIEA (d 0.742; 0.103 mL, 0.590 mmol) were then added, and the reaction was stirred at room temperature for 2 hours. The reaction was then quenched with saturated Na2CO3 and extracted with DCM. The product was dried, filtered, and concentrated to give the crude product. The crude product was purified (500:5 DCM:MeOH) to yield (S)-tert-butyl 2-(4-chlorophenyl)-3-(4-(5-(3-methoxyphenyl)-1H-pyrrolo[2, 3-1)]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (0.040 g, 53.6% yield).

1. customThe reaction was then quenched with saturated Na2CO3
2. extractionextracted with DCM
3. customThe product was dried
4. filtrationfiltered
5. concentrationconcentrated
6. customto give the crude product
7. customThe crude product was purified (500:5 DCM:MeOH)

ORD record

ord-8b5c5a1979c64d1da5f9468769b01d9f

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841304B2