HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → N-(4-(1-hydroxycyclohexyl)benzyl)-2-methyl-1,8-naphthyridine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 2-Methyl-1,8-naphthyridine-3-carboxylic acid | HCID 2736908 | — |
| Reactant | 1-(4-(Aminomethyl)phenyl)cyclohexanol | HCID 66633231 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | N-(4-(1-hydroxycyclohexyl)benzyl)-2-methyl-1,8-naphthyridine-3-carboxamide | HCID 46908389 | 17.5% |
Reaction Steps
144 mg (0.76 mmol) 2-methyl-1,8-naphthyridine-3-carboxylic acid and 136 mg (0.84 mmol) CDI were refluxed in 5 ml EtOAc for 2 h. The solution was cooled to r.t. and 157 mg (0.76 mmol) 1-(4-(aminomethyl)phenyl)cyclohexanol followed by 5 ml CH2Cl2 was added. The mixture was stirred for 2 days at r.t. Concentrated to dryness and purified by flash chromatography (SiO2, CH2Cl2/MeOH 20:1→10:1) to afford 50 mg (13%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415333B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-0f45341a03c241dd946181785bb94778 |
| Source note | uspto-grants-2013_04 |