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

HRID 1622724

Reaktionsgleichung

Reaktionsgleichung von HRID 1622724
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH2:10]([C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=1)[O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:17]=1)[CH3:11]>C1COCC1>[CH2:10]([C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][CH:31]=1)[O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:23]3=[N:28][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:24]3[CH:25]=[CH:26][CH:27]=2)=[CH:20][CH:21]=1)[CH3:11]

Komponenten

5

Edukt 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667487013-(4-(3-Ethylphenoxy)phenyl)pyridin-2-amine

Produkt 1

HCID 667481449-[4-(3-Ethylphenoxy)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%, 215 mg) in THF (dry) (20 mL) was added 2-chloroethanesulfonyl chloride (0.339 mL) at 0° C. and the mixture was stirred for 5 min at the same temperature. A solution of 3-(4-(3-ethylphenoxy)phenyl)pyridin-2-amine (312 mg) in THF (dry) (30 mL) was added at 0° C. and the mixture was stirred at room temperature for 1 hr. The mixture was quenched with water at 0° C. Water and EtOAc/THF were added and the extracted organic layer was washed with brine. Silica-gel was added to the organic layer and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and washed with IPE/EtOAc to give the title compound (295 mg) as a white solid. A part of this was recrystallized from THF/IPE.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. customThe mixture was quenched with water at 0° C
  3. additionWater and EtOAc/THF were added
  4. washthe extracted organic layer was washed with brine
  5. additionSilica-gel was added to the organic layer
  6. customthe volatiles were removed in vacuo
  7. customwas purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  8. washwashed with IPE/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-d5214fef3bea41b7b7cf7988427bbdcb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778934B2

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