HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 68761488, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | N-((1,1-dimethylethoxy)carbonyl)-beta-alanine | HCID 76809 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | 5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochloride | HCID 68758780 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68761488 | HCID 68761488 | 43% |
Reaction Steps
5-Phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyri dine dihydrochloride (0.10 g, 0.285 mmol, see Example 19), 3-(tert-butoxycarbonylamino)propanoic acid (0.0646 g, 0.342 mmol), HOBT-H2O (0.0610 g, 0.399 mmol), and EDCI (0.0709 g, 0.370 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.248 mL, 1.42 mmol) was then added, and the reaction was stirred at room temperature for 18 hours. The reaction was then poured into Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, concentrated and purified (500:10 DCM:MeOH) to give tert-butyl 3-oxo-3-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propylcarbamate (0.055 g, 43.0% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08841304B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-43dd75321c944660a715c46eb82c9e26 |
| Source note | uspto-grants-2014_09 |