9-{4-[3-(1,1-Difluoroethyl)phenoxy]phenyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide → 9-{4-[3-(1,1-Difluoroethyl)phenoxy]phenyl}-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 2035905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2035905
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][CH:29]=1)[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:20]3=[N:21][S:22](=[O:26])(=[O:25])[CH2:23][CH2:24][N:19]3[CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)([F:4])[CH3:3]>C1COCC1.CO.[Pt](=O)=O>[F:4][C:2]([C:5]1[CH:6]=[C:7]([CH:27]=[CH:28][CH:29]=1)[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]2[C:20]3=[N:21][S:22](=[O:26])(=[O:25])[CH2:23][CH2:24][N:19]3[CH2:18][CH2:17][CH2:16]2)=[CH:13][CH:14]=1)([F:1])[CH3:3]

Komponenten

5

Edukt 1

HCID 667487699-{4-[3-(1,1-Difluoroethyl)phenoxy]phenyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Produkt 1

HCID 667486239-{4-[3-(1,1-Difluoroethyl)phenoxy]phenyl}-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 345198Adams' catalystKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Platinum(IV) oxide (30 mg) was added to a solution of 9-{4-[3-(1,1-difluoroethyl)phenoxy]phenyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (230 mg) in THF (dry) (20 mL) and MeOH (20 mL). The mixture was stirred at room temperature under hydrogen overnight. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc) and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) and concentrated. The residue was crystallized from EtOAc/hexane to give the title compound (79.4 mg) as colorless crystals.

Aufarbeitung

  1. additionActivated carbon was added
  2. customthe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
  5. concentrationconcentrated
  6. customThe residue was crystallized from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-4ff00fc45f2d4c27ac7f7035ff8ec86c
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575154B2

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