HCID 66747700, Verbindung → 9-[4-(4-Fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1748029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748029
[F:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18]4=[N:19][S:20](=[O:24])(=[O:23])[CH2:21][CH2:22][N:17]4[CH:16]=[C:15]([CH3:25])[CH:14]=3)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[O:28][CH3:29]>C1COCC1.CO.[Pt](=O)=O>[F:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH:13]3[C:18]4=[N:19][S:20](=[O:24])(=[O:23])[CH2:21][CH2:22][N:17]4[CH2:16][CH:15]([CH3:25])[CH2:14]3)=[CH:11][CH:12]=2)=[CH:4][C:3]=1[O:28][CH3:29]

Komponenten

5

Edukt 1

HCID 66747700HCID 66747700, Verbindung

Produkt 1

HCID 667480489-[4-(4-Fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideAusbeute 7,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 345198Adams' catalystKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Platinum(IV) oxide (30 mg) was added to a solution of 9-[4-(4-fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (400 mg) in THF (dry) (15 mL) and MeOH (15 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 (30 mg) was added and the mixture was stirred at room temperature under hydrogen overnight. AcOH (10 mL) and platinum(IV) oxide (30 mg) were added and the mixture was stirred at room temperature under hydrogen for 1 day and at 50° C. for 1 day. 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 purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo. The residue was crystallized from THF/IPE to give the title compound (30.3 mg) as colorless crystals.

Aufarbeitung

  1. additionActivated carbon was added
  2. customthe insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc)
  3. additionPlatinum(IV) oxide (30 mg) was added
  4. stirringthe mixture was stirred at room temperature under hydrogen overnight
  5. additionAcOH (10 mL) and platinum(IV) oxide (30 mg) were added
  6. stirringthe mixture was stirred at room temperature under hydrogen for 1 day and at 50° C. for 1 day
  7. additionActivated carbon was added
  8. customthe insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc)
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  11. concentrationconcentrated in vacuo
  12. customThe residue was crystallized from THF/IPE

Quellen und Nachweise

ORD-Eintrag
ord-31999f6f91c24b7f9171ce7e1bd45e3d
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150591B2

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