2-(4-Hydroxyphenyl)acetohydrazide → 4-(6-Thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-phenol

HRID 1661792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1661792
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:6][CH:7]=1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([NH:23][NH2:24])=O)=[CH:16][CH:15]=1>C(O)CCC>[S:9]1[CH:10]=[CH:11][CH:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]2[N:3]([C:21]([CH2:20][C:17]3[CH:18]=[CH:19][C:14]([OH:13])=[CH:15][CH:16]=3)=[N:23][N:24]=2)[N:4]=1

Komponenten

4

Edukt 2

HCID 37318662-(4-Hydroxyphenyl)acetohydrazideHCID 64047013-Chloro-6-(thiophen-2-yl)pyridazine

Produkt 1

HCID 167360634-(6-Thiophen-2-yl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A solution containing 3-Chloro-6-thiophene-2-yl-pyridazine (58 mg, 0.29 mmol) Example 17: step a and (4-Hydroxy-phenyl)-acetic acid hydrazide (120 mg, 0.58 mmol) in butanol (5 mL) was heated to reflux overnight. The reaction was cooled to rt and the solids were filtered and washed with MeOH. The solid was recrystalized from MeOH to yield the title compound as a tan solid. 1H-NMR (CD3OD/CDCl3): δ 8.12-8.10 (1H, d, J=9.34 Hz), 7.83-7.82 (1H, d, J=3.7 Hz), 7.78-7.76 (1H, d, J=9.8 Hz), 7.67-7.65 (1H, d, J=5.0 Hz), 7.34-7.32 (2H, d, J=6.5 Hz), 7.22-7.21 (1H, m), 6.77-6.75 (2H, d, J=8.3 Hz), 4.49 (2H, s). ESI-MS (m/z): Calcd. For C16H12N4OS: 308.07; found: 309.2 (M+H).

Aufarbeitung

  1. temperatureto reflux overnight
  2. filtrationthe solids were filtered
  3. washwashed with MeOH
  4. customThe solid was recrystalized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-e62c45a77aae46c89e42c173102330df
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030305B2

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