HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Toreforant
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | HCID 6775 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (2-Amino-3,5-dimethylphenyl)amine | HCID 3613321 | — |
| Reactant | 4-Methyl-2-((3-(1-methylpiperidin-4-yl)propyl)amino)pyrimidine-5-carbaldehyde | HCID 46221560 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | Toreforant | HCID 23650961 | — |
Reaction Steps
To a 4 mL vial were added 3,5-dimethyl-benzene-1,2-diamine.2HCl (69 mg, 0.33 mmol), 4-methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbaldehyde (92 mg, 0.33 mmol), 2,3-dichloro-5,6-dicyano-p-benzoquinone (75 mg, 0.33 mmol), and DMF (2 mL). After addition of triethylamine (0.09 mL, 0.66 mmol), the resultant mixture was stirred for 5 hours at room temperature. The resultant mixture was then diluted with 1N NaOH (7.5 mL) and dichloromethane (7.5 mL). The organic layer was concentrated and purified by flash chromatography to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09371311B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-c3e5fce53e3c4d97a5e4f3f85c089dae |
| Source note | uspto-grants-2016_06 |