Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 10023092 | HCID 10023092 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Chloroform isopropyl alcohol | HCID 21906603 | — |
| Product | HCID 58916337 | HCID 58916337 | 68% |
Reaction Steps
Cool a solution of 2-{7-[2-[6-methyl-(pyridin-2-yl)]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-quinoxalin-2-yloxy}-ethanol (0.5 g, 1.3 mmol) and diisopropylamine (0.5 ml) in dry dichloromethane (10 mL) to −30° C. Add methanesulfonylchloride (0.5 ml) dropwise to the solution and stir the resulting mixture for 30 min while allowing the reaction mixture to warm to room temperature. Add 5 N hydrochloric acid (0.2 mL) and pyridine (1 mL) to the mixture and heat at 80° C. for 3 h. Dilute the reaction mixture with 1:1 chloroform/isopropyl alcohol and wash the solution with saturated sodium chloride solution. Dry the organic layer (sodium sulfate), filter, and evaporate the solvents. Purify the residue by silica gel chromatography (dichloromethane to 1:1 dichloromethane/methanol) to give 274 mg (68%) of the titled compound. MS ES+ 407 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07368445B2 |
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| Source dataset | uspto-grants-2008_05 |
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| ORD ID | ord-15073be77e1c4664b382a87a733962ca |
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| Source note | uspto-grants-2008_05 |
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