N'-(6-Chloropyridazin-3-yl)-2-(quinolin-6-yl)acetohydrazide → 6-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

HRID 1959640

Reaction equation

HRID 1959640 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][NH:9][C:10](=O)[CH2:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[CH:15]3)=[CH:4][CH:3]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][CH:16]=[CH:15]4)=[N:9][N:8]=2)[N:7]=1

Participants

3

Reactant 1

HCID 86652010N'-(6-Chloropyridazin-3-yl)-2-(quinolin-6-yl)acetohydrazide

Product 1

HCID 249683676-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinolineYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N′-(6-chloropyridazin-3-yl)-2-(quinolin-6-yl)acetohydrazide (8 g crude, 25.5 mmol) in 250 mL of acetic acid was heated at 50° C. for 5 h. After the reaction was complete, the solvent was evaporated and the residue was taken up in EtOAc. The formed solid (mainly dicyclohexyl urea) was filtered off and the filtrate was evaporated to afford the title compound as yellow solid (4 g, 53%). 1H-NMR (400 MHz, MeOH-d4) δ ppm 8.82 (d, 1H), 8.33 (d, 1H), 8.25 (d, 1H), 8.0 (d, 1H), 7.93 (s, 1H), 7.83 (d, 1H), 7.53 (m, 1H), 7.42 (d, 1H), 4.79 (s, 2H). LCMS (method B): [MH]+=296.0, tR=1.876 min.

Workup

  1. customthe solvent was evaporated
  2. filtrationThe formed solid (mainly dicyclohexyl urea) was filtered off
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b06e3b1f10274c0b91fd3d1cbf2e6347
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Linked notes

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