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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1945451Generated: October 25, 2026

Methanol → 5-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-nicotinamide

https://huagongshe.com/reaction/1945451

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
Reactant3-Pyridinecarboxamide, 5-amino-HCID 173747—
ReactantPMID26882240-Compound-8HCID 625381—
ReactantPyBOPHCID 2724699—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventDimethylformamideHCID 6228—
Product5-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-nicotinamideHCID 4444326261.6%

Reaction Steps

To solution of (4-adamantan-1-yl-phenoxy)-acetic acid (50 mg, 0.17 mmol), 5-amino nicotinamide (47.89 mg, 0.34 mmol) and DMAP (42.71 mg, 0.34 mmol) in DMF 5 ml was added PyBOP (181 mg, 0.34 mmol), and stirred room temperature. Reaction mixture was poured onto ice cold water, diluted by methanol/MC mixture (10%). The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by preparative-TLC(CH2Cl2:MeOH=6:1) to afford 5-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-nicotinamide as a colorless solid (42.48 mg, 60% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08394799B2
Source datasetuspto-grants-2013_03
ORD IDord-e31ee4cd4d2e4ba482ec8db65f93a4ee
Source noteuspto-grants-2013_03