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Triethylamine → (9S)-9-[4-(4-chlorophenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 1622746
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1622746
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.[O:18]=[S:19]1(=[O:36])[CH2:24][CH2:23][N:22]2[CH2:25][CH2:26][CH2:27][C@@H:28]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)[C:21]2=[N:20]1>CN(C=O)C.C(O[Cu]OC(=O)C)(=O)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:35][C:32]2[CH:31]=[CH:30][C:29]([C@H:28]3[C:21]4=[N:20][S:19](=[O:36])(=[O:18])[CH2:24][CH2:23][N:22]4[CH2:25][CH2:26][CH2:27]3)=[CH:34][CH:33]=2)=[CH:11][CH:10]=1
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 742994-Chlorophenylboronic acid2×HCID 667484964-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol

Produkt 1

HCID 66748008(9S)-9-[4-(4-chlorophenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideAusbeute 15,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178476681
HCID 178476681, Verbindung
Katalysator
2×
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Diacetoxycopper (1037 mg) was added to a mixture of triethylamine (1.983 mL), 4-chlorophenylboronic acid (1339 mg), 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol (800 mg) and in DMF (dry) (30 ml). The mixture was stirred at room temperature under a dry atmosphere with anhydrous calcium chloride tube for 15 hr. Then 4-chlorophenylboronic acid (1339 mg) and diacetoxycopper (1037 mg) were added and the mixture was stirred at room temperature under a dry atmosphere with anhydrous calcium chloride tube for 2 days. The insoluble material was removed by filtration, and the filtrate was diluted with water, and extracted with EtOAc. The organic layer was washed with 0.1N NaOH aq., dried over anhydrous magnesium sulfate. Silica-gel was added 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) then crystallized from THF/IPE to give the title compound (177 mg) as an off-white solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature under a dry atmosphere with anhydrous calcium chloride tube for 2 days
  2. customThe insoluble material was removed by filtration
  3. additionthe filtrate was diluted with water
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with 0.1N NaOH aq.
  6. dry with materialdried over anhydrous magnesium sulfate
  7. additionSilica-gel was added
  8. customthe volatiles were removed in vacuo
  9. customwas purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  10. customthen crystallized from THF/IPE

Quellen und Nachweise

ORD-Eintrag
ord-be20fcd16e224cb3af2b301344eacc7f
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08778934B2

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