Tetrabutylammonium Fluoride → 4-[4-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenoxy]phenol

HRID 1405876Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1405876
[Si]([O:8][C:9]1[CH:33]=[CH:32][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:25]4=[N:26][S:27](=[O:31])(=[O:30])[CH2:28][CH2:29][N:24]4[CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[O:31]=[S:27]1(=[O:30])[CH2:28][CH2:29][N:24]2[CH:23]=[CH:22][CH:21]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([O:13][C:12]4[CH:32]=[CH:33][C:9]([OH:8])=[CH:10][CH:11]=4)=[CH:15][CH:16]=3)[C:25]2=[N:26]1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 667481279-[4-(4-{[Tert-butyl(dimethyl)silyl]oxy}phenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

Produkt 1

HCID 668239904-[4-(2,2-Dioxido-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenoxy]phenolAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 9-[4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (1.82 g) in THF (dry) (55 mL) was added to tetrabutylammonium fluoride(1 M in THF) (6.79 mL) at room temperature. After stirring for 0.5 hr, the mixture was added with sat.NH4Cl aq. and silica gel, then concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane then MeOH in EtOAc), recrystallized from THF—IPE, then preparative HPLC (C18, eluent; H2O/MeCN with 0.1% TFA). The collected fraction was concentrated in vacuo. The residue was recrystallized from MeCN—H2O to give the title compound (492 mg) as a white solid.

Aufarbeitung

  1. additionthe mixture was added
  2. concentrationNH4Cl aq. and silica gel, then concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel
  4. washeluted with EtOAc in hexane
  5. customMeOH in EtOAc), recrystallized from THF—IPE
  6. concentrationThe collected fraction was concentrated in vacuo
  7. customThe residue was recrystallized from MeCN—H2O

Quellen und Nachweise

ORD-Eintrag
ord-adc301a83f2a4b2bb775ea718d0eca1a
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916551B2

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