HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilyl isocyanate → 3-((r)-3-(5-Cyanopyridin-2-ylamino)pyrrolidine-1-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilyl isocyanate | HCID 70696 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (3R)-N-(8-azabicyclo[3.2.1]octan-3-yl)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamide dihydrochloride | HCID 66884619 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-((r)-3-(5-Cyanopyridin-2-ylamino)pyrrolidine-1-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxamide | HCID 66883448 | — |
Reaction Steps
To a stirred solution of (3R)—N-(8-azabicyclo[3.2.1]octan-3-yl)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamide dihydrochloride salt (17.5 mg, 0.042 mmol) and i-Pr2NEt (0.032 mL, 0.18 mmol) in CH2Cl2 (1 mL) was added Me3SiNCO (0.008 mL, 0.06 mmol). The mixture was stirred at overnight and concentrated. The residue was purified by prep HPLC to give two isomeric products.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08828985B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-589c675f5f1e4a23a292f586aad512f3 |
| Source note | uspto-grants-2014_09 |