HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → 6-Amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 4-(3-Bromo-phenylamino)-6-(4-methoxy-benzylamino)-[1,7]naphthyridine-3-carbonitrile | HCID 12969105 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 6-Amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile | HCID 9798006 | 84.6% |
Reaction Steps
To 400 mg of 4-(3-bromo-phenylamino)-6-(4-methoxy-benzylamino)-[1,7]naphthyridine-3-carbonitrile in 10 mL of methylene chloride was added 10 mL of trifluoroacetic acid. After stirring under an inert atmosphere for 20 hours, 10 mL of toluene was added and the solvents were stripped on a rotary evaporator. The product was purified by flash chromatography with a gradient of 0-5% methanol/chloroform to give 250 mg of 6-amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile as an off-white solid: melting point 185-190° C. (decomposed); mass spectrum (m/e): M+H 340.0, 342.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06548496B2 |
| Source dataset | uspto-grants-2003_04 |
| ORD ID | ord-b112f7fdb3244175b4bd717f07911945 |
| Source note | uspto-grants-2003_04 |