HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → Methanesulfonamide, N-(3-((4R)-4-(3,3-dimethylbutyl)-3,4-dihydro-1-hydroxy-4-methyl-3-oxo-2-naphthalenyl)-1,1-dioxido-2H-1,2,4-benzothiadiazin-7-yl)-
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | (1r)-3-(7-Amino-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-1-(3,3-dimethylbutyl)-4-hydroxy-1-methylnaphthalen-2(1h)-one hydrochloride | HCID 135869464 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | Methanesulfonamide, N-(3-((4R)-4-(3,3-dimethylbutyl)-3,4-dihydro-1-hydroxy-4-methyl-3-oxo-2-naphthalenyl)-1,1-dioxido-2H-1,2,4-benzothiadiazin-7-yl)- | HCID 135430231 | — |
Reaction Steps
A solution of Example 49G (0.250 g, 0.510 mmol), mesyl chloride (0.158 mL, 2.04 mmol), and pyridine (0.330 mL, 4.08 mmol) in acetone (3 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 a yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07538105B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-30190dc9ede9420ea41f123eb151f71c |
| Source note | uspto-grants-2009_05 |