HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → HCID 11706659, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | N-{2-[(4-butylphenyl)ethynyl]benzyl}-1-hexanamine | HCID 57554480 | — |
| Reactant | 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carboxylic acid | HCID 57554489 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 11706659 | HCID 11706659 | 87% |
Reaction Steps
A solution of N-{2-[(4-butylphenyl)ethynyl]benzyl}-1-hexanamine (174 mg, 0.50 mmol), 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carboxylic acid (122 mg, 0.55 mmol), EDC.HCl (115 mg, 0.60 mmol), DIEA (102 μl, 0.60 mmol) and HOBT (81 mg, 0.60 mmol) in DCM (10 mL) was stirred at rt for 3 hrs. The reaction mixture was diluted with DCM and washed with a saturated aqueous solution of NaHCO3, an aqueous solution of HCl (1N) and brine. The organic layer was dried over MgSO4 and the solvent Was removed under reduced pressure. Purification by flash chromatography on silicagel (EtOAc/c-Hex (20/80)) gave 238 mg (87%) of the title compound. HPLC, Rt: 6.14 min (purity: 86.7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07947851B2 |
| Source dataset | uspto-grants-2011_05 |
| ORD ID | ord-27d98cd59e22490ca635f05b78ee6c2a |
| Source note | uspto-grants-2011_05 |