HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclopropanecarbonyl chloride → N'-(Cyclopropylcarbonyl)-1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclopropanecarbonyl chloride | HCID 77637 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1-Ethyl-4-((tetrahydro-2H-pyran-4-yl)amino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide dihydrochloride | HCID 53487828 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N'-(Cyclopropylcarbonyl)-1-ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridine-5-carbohydrazide | HCID 57675148 | 45% |
Reaction Steps
A solution of Intermediate 19 (0.045 g) in THF (2 ml) was treated with DIPEA (0.045 ml), then with cyclopropylcarbonyl chloride (0.013 g) and stirred at room temperature for 16 h. The mixture was concentrated in vacuo and the residue partitioned between dichloromethane and water. The layers were separated and the organic layer concentrated in vacuo, then applied to an SPE cartridge (aminopropyl, 1 g). The column was eluted with methanol to afford Intermediate 20 as a white solid (0.02 g). LCMS showed MH+=373; TRET=2.15 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07528148B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-5644c95b75ba4d8da6d565b0e8131feb |
| Source note | uspto-grants-2009_05 |