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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 72145Generated: October 28, 2026

Trimethylsilyl isocyanate → 3-((r)-3-(5-Cyanopyridin-2-ylamino)pyrrolidine-1-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxamide

https://huagongshe.com/reaction/72145

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrimethylsilyl isocyanateHCID 70696—
ReactantDiisopropylethylamineHCID 81531—
Reactant(3R)-N-(8-azabicyclo[3.2.1]octan-3-yl)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamide dihydrochlorideHCID 66884619—
SolventDichloromethaneHCID 6344—
Product3-((r)-3-(5-Cyanopyridin-2-ylamino)pyrrolidine-1-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxamideHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08828985B2
Source datasetuspto-grants-2014_09
ORD IDord-589c675f5f1e4a23a292f586aad512f3
Source noteuspto-grants-2014_09