Acetic Acid → HCID 59716656, Verbindung

HRID 2224225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2224225
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][N:12]1[C:34](=[O:35])[N:15]2[N:16]=[CH:17][C:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[C:19]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[C:14]2=[N:13]1)(=O)C.O(C)[Na].C(O)(=O)C>CO>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][N:12]1[C:34](=[O:35])[N:15]2[N:16]=[CH:17][C:18]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[C:19]([C:20]3[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=3)[C:14]2=[N:13]1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 59716641HCID 59716641, Verbindung2×HCID 178418582HCID 178418582, Verbindung

Produkt 1

HCID 59716656HCID 59716656, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

2-((7,8-Bis(4-chlorophenyl)-3-oxo-[1,2,4]triazolo[4,3-b]pyridazin-2(3H)-yl)methyl)phenyl acetate, prepared as described in 25A, (1.13 g), was dissolved in 25 mL of CH3OH. A solution of NaOCH3 (121 mg, 2.24 mmol) in a small amount of CH3OH (2 mL) was added to the reaction, and then, the reaction was stirred overnight. After this time, 0.3 mL of acetic acid was added to the reaction. The reaction was stirred for an additional 10 min, and then the resultant solution was concentrated under reduced pressure. The crude residue was purified using silica gel column chromatography using an automated system, eluting with a gradient of 0% to 60% EtOAc/hexanes for 30 min followed by 60% EtOAc/hexanes for an additional 15 min. The title compound, 2-(2-hydroxybenzyl)-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (818 mg, 79% yield) was obtained as yellow solid. MS [M+H]+=463; 1H NMR (CDCl3, 400 MHz) δ 8.54 (s, 1H), 8.14 (s, 1H), 7.32-7.17 (m, 8H), 7.04-7.00 (m, 2H), 6.94 (dd, 1H), 6.81 (td, 1H), 5.13 (s, 2H).

Aufarbeitung

  1. stirringThe reaction was stirred for an additional 10 min
  2. concentrationthe resultant solution was concentrated under reduced pressure
  3. customThe crude residue was purified
  4. washeluting with a gradient of 0% to 60% EtOAc/hexanes for 30 min
  5. waitfollowed by 60% EtOAc/hexanes for an additional 15 min

Quellen und Nachweise

ORD-Eintrag
ord-d9139a734ea944ada14ef0b19cb37de8
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07378418B2

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