HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 5-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-nicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | 3-Pyridinecarboxamide, 5-amino- | HCID 173747 | — |
| Reactant | PMID26882240-Compound-8 | HCID 625381 | — |
| Reactant | PyBOP | HCID 2724699 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-[2-(4-Adamantan-1-yl-phenoxy)-acetylamino]-nicotinamide | HCID 44443262 | 61.6% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394799B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-e31ee4cd4d2e4ba482ec8db65f93a4ee |
| Source note | uspto-grants-2013_03 |