HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → N-[3-(4-butyl-1-hydroxy-4-methyl-3-oxo-2-naphthyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | 3-(7-Amino-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-1-butyl-4-hydroxy-1-methylnaphthalen-2(1h)-one hydrochloride | HCID 136403739 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | N-[3-(4-butyl-1-hydroxy-4-methyl-3-oxo-2-naphthyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide | HCID 135440188 | 96% |
Reaction Steps
A solution of Example 33B (0.052 g, 0.112 mmol), mesyl chloride (0.035 mL, 0.447 mmol), and pyridine (0.073 mL, 0.893 mmol) in acetone (1.5 mL) was stirred at 25° C. for 18 hours. The solution was partitioned between ethyl acetate and dilute citric acid and the layers were separated. The ethyl acetate layer was dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with methylene chloride and 2.5% methanol in methylene chloride to give the desired product (0.054 g, 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07538105B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-98eb17253bb7421f96b5620482a61fe8 |
| Source note | uspto-grants-2009_05 |