HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → 6-(1-Anthraquinonecarbonyl)-3,10-bis (2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicylo[10.3.1]hexadeca-1(16),12,14-triene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 2-Anthraquinonecarboxylic acid | HCID 67030 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | HCID 10555399 | HCID 10555399 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 6-(1-Anthraquinonecarbonyl)-3,10-bis (2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicylo[10.3.1]hexadeca-1(16),12,14-triene | HCID 21257333 | 76% |
Reaction Steps
The title compound was prepared following the procedures illustrated above in Example 75 using 3,10-bis (2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo-[10.3.1]hexadeca-1(16),12,14-triene (1.0 g, 1.7 mmol), anthraquinone-2-carboxylic acid (0.43 g, 1.7 mmol), DCC (0.35 g, 1.7 mmol), HOBT (0.23 g, 1.7 mmol) and 4-methylmorpholine (0.25 g, 2.5 mmol) in 10 mL of anhydrous THF and 20 mL of anhydrous DMF in 56 h. The compound was purified by flash chromatography on a silica gel column using 200:1 CH2Cl2—MeOH as an eluent to give 1.06 g (76%) of the title compound as a pale yellow foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06191273B1 |
| Source dataset | uspto-grants-2001_02 |
| ORD ID | ord-45b22fedd8d549d0b0b74ce51cdd5c54 |
| Source note | uspto-grants-2001_02 |