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

HRID 1622755

Reaktionsgleichung

Reaktionsgleichung von HRID 1622755
[H-].[Na+].Cl[CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[CH2:10]([C:12]1[CH:31]=[CH:30][C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]([NH2:29])=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)=[CH:14][CH:13]=1)[CH3:11]>C1COCC1>[CH2:10]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24]4=[N:29][S:6](=[O:8])(=[O:7])[CH2:5][CH2:4][N:25]4[CH:26]=[CH:27][CH:28]=3)=[CH:19][CH:18]=2)=[CH:30][CH:31]=1)[CH3:11]

Komponenten

5

Edukt 3

HCID 15385Ethanesulfonylchloride, 2-chloro-HCID 24758Sodium hydrideHCID 667482393-(4-(4-Ethylphenoxy)phenyl)pyridin-2-amine

Produkt 1

HCID 667476499-[4-(4-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%, 81 mg) in THF (dry) (10 mL) was added 2-chloroethanesulfonyl chloride (0.085 mL) at 0° C. and the mixture was stirred for 10 min at the same temperature. A solution of 3-(4-(4-ethylphenoxy)phenyl)pyridin-2-amine (117 mg) in THF (dry) (10 mL) was added at 0° C. and the mixture was stirred at room temperature under nitrogen for 4 hr. The mixture was quenched with water at 0° C. Water, EtOAc and THF were added and the mixture was extracted. 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) and concentrated in vacuo to give 9-[4-(4-ethylphenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide as a white solid. Platinum(IV) oxide (20 mg) was added to a solution of 9-[4-(4-ethylphenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (153 mg) in THF (dry) (20 mL) and MeOH (20 mL). The mixture was stirred at room temperature under hydrogen for 3 hr. Activated carbon was added and the insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc). Platinum(IV) oxide (20 mg) was added and the mixture was stirred at room temperature under hydrogen overnight. Activated carbon was added and the insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc) and the filtrate was concentrated in vacuo. The residue was crystallized from THF/IPE to give the title compound (46.7 mg) as colorless crystals.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c476f1f93a574b22bd7f389a3d1f0596
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778934B2

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