6-(2-Benzylidenehydrazinyl)-3-chloro-4-(pyrrolidin-1-yl)pyridazine → 6-Chloro-3-phenyl-7-(1-pyrrolidinyl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 47229Notes

Reaction equation

HRID 47229 reaction equation
[CH:1](=[N:8][NH:9][C:10]1[N:11]=[N:12][C:13]([Cl:21])=[C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C>C(O)(=O)C>[Cl:21][C:13]1[C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:15][C:10]2[N:11]([C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:8][N:9]=2)[N:12]=1

Participants

4

Reactant 2

HCID 739942816-(2-Benzylidenehydrazinyl)-3-chloro-4-(pyrrolidin-1-yl)pyridazineHCID 178418268HCID 178418268, compound

Product 1

HCID 227441646-Chloro-3-phenyl-7-(1-pyrrolidinyl)-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A slurry of N-benzylidene-N′-[6-chloro-5-(pyrrolidin-1-yl)pyridazin-3-yl]hydrazine (14 g, 0.046 mol) and lead(IV) acetate (24 g, 0.055 mol) in acetic acid (300 ml) was stirred at 60° C. under nitrogen overnight. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel, eluting with 0-10% methanol in ethyl acetate. The title compound was isolated as a yellow solid (4.1 g, 30%). 1H NMR (250 MHz, CDCl3) δ2.05 (4H, m), 3.56 (4H, m), 7.05 (1H, s), 7.51 (3H, m), 8.42 (2H, m). MS (ES+) m/e 300 [MH]+, 302 [MH]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluting with 0-10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-03f07d74493e4082b49c4341b77c0da4
Source dataset
uspto-grants-2004_03
Patent number
US06699859B1

Reaction notes

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