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

HRID 1661792Notes

Reaction equation

HRID 1661792 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-e62c45a77aae46c89e42c173102330df
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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