HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoic Acid → 1-[4-[2-(Tert-butoxycarbonylamino)pyridin-5-yl]benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoic Acid | HCID 243 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 22710058 | HCID 22710058 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-[4-[2-(Tert-butoxycarbonylamino)pyridin-5-yl]benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine | HCID 22709456 | 90% |
Reaction Steps
In a mixed solvent of dichloromethane (20 ml) and N,N-dimethylformamide (1 ml), 4-[2-(tert-butoxycarbonyl)amino]pyridin-5-yl]benzoic acid (74 mg) and 1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine trifluoroacetate (110 mg) were suspended. To the resulting suspension, 1-hydroxybenzotriazole (35 mg) and N-methylmorpholine (34 μl) were added, followed by the addition of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (68 mg) under ice cooling. After stirring at room temperature for 6 hours, the solvent was distilled off. The residue was purified by chromatography on a silica gel column (1% methanol-dichloromethane). The solvent was then distilled off, whereby the title compound (128 mg, 90%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06525042B1 |
| Source dataset | uspto-grants-2003_02 |
| ORD ID | ord-9ba9bd7221d14b5f8db98e063cafe615 |
| Source note | uspto-grants-2003_02 |