HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 71280017, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 2-amino-2-methylpropanenitrile hydrochloride | HCID 12239465 | — |
| Reactant | 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid | HCID 71280096 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71280017 | HCID 71280017 | 31% |
Reaction Steps
A mixture of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.07 g, 0.3 mmol), 2-amino-2-methylpropanenitrile hydrochloride (0.05 g, 0.42 mmol), EDCI (0.057 g, 0.3 mmol), DMAP (0.037 g, 0.3 mmol), and DIPEA (0.163 g, 1.26 mmol) in 10 mL of DMF were stirred at room temperature for 5 hours. Then HATU (0.114 g, 0.3 mmol) was added, the final reaction mixture was stirred for additional 15 hours. The solvent was removed under reduced pressure at 70° C., then the residue was triturated with water and ethyl acetate successively then decanted and dried to give 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(2-cyanopropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.026 g, 31%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08658646B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-dd40738205114787aea8fe436c9475ca |
| Source note | uspto-grants-2014_02 |