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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

HRID 494529
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 494529
Cl.[NH2:2][C:3]1[CH:31]=[CH:30][C:6]2[NH:7][C:8]([C:13]3[C:14](=[O:29])[C:15]([CH2:25][CH2:26][CH2:27][CH3:28])([CH3:24])[C:16]4[C:21]([C:22]=3[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[S:32](Cl)([CH3:35])(=[O:34])=[O:33].N1C=CC=CC=1>CC(C)=O>[CH2:25]([C:15]1([CH3:24])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]([OH:23])=[C:13]([C:8]2[NH:7][C:6]3[CH:30]=[CH:31][C:3]([NH:2][S:32]([CH3:35])(=[O:34])=[O:33])=[CH:4][C:5]=3[S:10](=[O:12])(=[O:11])[N:9]=2)[C:14]1=[O:29])[CH2:26][CH2:27][CH3:28]
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Komponenten

5

Edukt 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 1364037393-(7-Amino-1,1-dioxido-4h-1,2,4-benzothiadiazin-3-yl)-1-butyl-4-hydroxy-1-methylnaphthalen-2(1h)-one hydrochloride

Produkt 1

HCID 135440188N-[3-(4-butyl-1-hydroxy-4-methyl-3-oxo-2-naphthyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180
Acetone
Lösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  1. customThe solution was partitioned between ethyl acetate and dilute citric acid
  2. customthe layers were separated
  3. dry with materialThe ethyl acetate layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with methylene chloride and 2.5% methanol in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-98eb17253bb7421f96b5620482a61fe8
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07538105B2

Notizen zur Reaktion

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