Sulfuric Acid → HCID 71128767, Verbindung

HRID 629866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629866
[F:1][C:2]1([F:33])[CH2:4][CH:3]1[CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([C:15]3[CH:16]4[CH2:22][CH2:21][CH:19]([CH:20]=3)[N:18](C3C=CC(OC)=CC=3)[CH2:17]4)=[CH:12][CH:13]=2)[N:8]([CH3:31])[C:7]1=[O:32].CC#N.OS(O)(=O)=O.I(O)(=O)(=O)=O>O>[CH:19]12[CH2:21][CH2:22][CH:16]([C:15]([C:11]3[N:10]=[C:9]4[N:8]([CH3:31])[C:7](=[O:32])[N:6]([CH2:5][CH:3]5[CH2:4][C:2]5([F:1])[F:33])[C:14]4=[CH:13][CH:12]=3)=[CH:20]1)[CH2:17][NH:18]2

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 65185Metaperiodic acidHCID 117702516HCID 117702516, Verbindung

Produkt 1

HCID 71128767HCID 71128767, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1-[(2,2-Difluorocyclopropyl)methyl]-5-[2-(4-methoxyphenyl)-2-azabicyclo-[2.2.2]oct-5-en-5-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (6-2, 52 mg, 0.12 mmol, 1.0 equiv) was added to CH3CN (1 mL) and water (1 mL). To this suspension was added aqueous H2SO4 (115 μL, 0.12 mmol, 1.0 equiv, 1.0 M) followed by periodic acid in one portion (26 mg, 0.12 mmol, 1.0 equiv). The reaction contents were heated to 50° C. for 18 h. Following this duration, LCMS showed consumption of starting material. The mixture was subsequently filtered through Celite, rinsed with CH3CN and purified by reverse-phase HPLC (10-90% CH3CN:H2O) to give 6-3 as an off-white solid. MS m/z (M+H): calculated=346.4; observed=347.1.

Aufarbeitung

  1. customThe reaction contents
  2. customconsumption of starting material
  3. filtrationThe mixture was subsequently filtered through Celite
  4. washrinsed with CH3CN
  5. custompurified by reverse-phase HPLC (10-90% CH3CN:H2O)

Quellen und Nachweise

ORD-Eintrag
ord-2d0c1f1e32624e0b9a65018c133ae9aa
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315518B2

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