HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → tert-butyl (3R,4R)-4-(6-chloro-5-cyanopyrazin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3,5-Dichloropyrazine-2-carbonitrile | HCID 52987744 | — |
| Reactant | tert-Butyl ((3R,4R)-4-aminotetrahydro-2H-pyran-3-yl)carbamate | HCID 68077633 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 2-Oxopropiononitrile | HCID 69430 | — |
| Product | tert-butyl (3R,4R)-4-(6-chloro-5-cyanopyrazin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate | HCID 86685613 | 119% |
Reaction Steps
To a mixture of 3,5-dichloropyrazine-2-carbonitrile (369 mg, 2.09 mmol) and tert-butyl (3R,4R)-4-aminotetrahydro-2H-pyran-3-ylcarbamate (500 mg, 2.3 mmol) in AcCN (7.5 mL) was added DIPEA (0.41 mL, 2.3 mmol). After stirring at room temperature for 5 h, it was diluted with EtOAc, washed with sat. NaHCO3, organic layer was separated and washed with brine, dried and concentrated to give tert-butyl (3R,4R)-4-(6-chloro-5-cyanopyrazin-2-ylamino)tetrahydro-2H-pyran-3-ylcarbamate (880 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359308B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-4ad0450049184a7da83cd70bef8e15f8 |
| Source note | uspto-grants-2016_06 |