Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-(Dimethylamino)propyl chloride hydrochloride | HCID 94308 | — |
| Reactant | HCID 178522861 | HCID 178522861 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 16073840 | HCID 16073840 | — |
Reaction Steps
A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 5 (0.458 g) is dissolved in DMF (10 mL), and K2CO3 (0.69 g) and 3-dimethylaminopropyl chloride hydrochloride (0.42 g) are added. The reaction mixture is heated to 90° C. for 6 h. Water is added and a dark solid formed, which is isolated by decanting the liquid. Column chromatography (elution with 1-20% MeOH/CHCl3) gave 0.103 g of a solid. Crystallization by dissolving in CH2Cl2 with a few drops of MeOH and adding to a 1:1 solution of pentane/Et2O gave 0.072 g of the title compound as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06248739B1 |
|---|
| Source dataset | uspto-grants-2001_06 |
|---|
| ORD ID | ord-c76c4f94149f4492a08de602bca1dfe6 |
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| Source note | uspto-grants-2001_06 |
|---|
