Ethanesulfonylchloride, 2-chloro- → 9-[4-(3,4-Dimethylphenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1405794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405794
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH3:10][C:11]1[CH:12]=[C:13]([CH:28]=[CH:29][C:30]=1[CH3:31])[O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22]([NH2:27])=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][CH:16]=1>C1COCC1>[CH3:10][C:11]1[CH:12]=[C:13]([CH:28]=[CH:29][C:30]=1[CH3:31])[O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22]3=[N:27][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:23]3[CH:24]=[CH:25][CH:26]=2)=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667485863-(4-(3,4-Dimethylphenoxy)phenyl)pyridin-2-amine

Produkt 1

HCID 667485539-[4-(3,4-Dimethylphenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of NaH (60%, 99 mg) in THF (dry) (10 mL) was added 2-chloroethanesulfonyl chloride (0.156 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-(3,4-dimethylphenoxy)phenyl)pyridin-2-amine (144 mg) in THF (dry) (10 mL) was added at 0° C. and the mixture was stirred at room temperature under nitrogen overnight. The mixture was quenched with water at 0° C. and extracted with EtOAc/THF. Silica-gel was added to the organic phase and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) to give the title compound (119.7 mg). A part of product was recrystallized from MeCN/IPE.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature under nitrogen overnight
  2. customThe mixture was quenched with water at 0° C.
  3. extractionextracted with EtOAc/THF
  4. additionSilica-gel was added to the organic phase
  5. customthe volatiles were removed in vacuo
  6. customwas purified by column chromatography (silica gel, eluted with MeOH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-7b23452fb883491091aad13a911b56e8
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916551B2

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