HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine, hydrochloride → 5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(3-(dimethylcarbamoyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-6-yl)pyrazolo[1,5-a]pyridine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine, hydrochloride | HCID 10473 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 89618999 | HCID 89618999 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)-N-(3-(dimethylcarbamoyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-6-yl)pyrazolo[1,5-a]pyridine-3-carboxamide | HCID 71599264 | — |
Reaction Steps
To a stirred solution of 6-(5-((R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyridine-3-carboxamido)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-carboxylic acid (45 mg, 0.08 mmol) in dry DMF (1 mL) was added EDCI (28.7 mg, 0.09 mmol), HOBt (12 mg, 0.88 mmol) and stirring was continued at 25° C. for 15 min. To the above reaction added dimethylamine hydrochloride (7.8 mg, 0.1 mmol) followed by DIPEA (0.05 ml, 0.26 mmol), stirring was continued at 25° C. for 16 h. Reaction mixture was diluted with DCM (50 mL), washed it with water followed by brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford title compound as white solid. MS (ESI): m/z 534.2 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09289419B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-e89c674daa5b4511b63eefefe27db880 |
| Source note | uspto-grants-2016_03 |