3,6-Dichloropyridazine → 6-(6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-5,7-difluoro-quinoline

HRID 1892445Notes

Reaction equation

HRID 1892445 reaction equation
[F:1][C:2]1[C:11]([CH2:12][C:13]([NH:15][NH2:16])=O)=[C:10]([F:17])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl:18][C:19]1[N:20]=[N:21][C:22](Cl)=[CH:23][CH:24]=1>C(O)CCC>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]2[N:15]([C:13]([CH2:12][C:11]3[C:2]([F:1])=[C:3]4[C:8](=[CH:9][C:10]=3[F:17])[N:7]=[CH:6][CH:5]=[CH:4]4)=[N:20][N:21]=2)[N:16]=1

Participants

4

Reactant 2

HCID 673313,6-DichloropyridazineHCID 57742344(5,7-Difluoro-quinolin-6-yl)-acetic acid hydrazide

Product 1

HCID 581906006-(6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-5,7-difluoro-quinolineYield 58.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (5,7-difluoro-quinolin-6-yl)-acetic acid hydrazide (1.024 g, 4.32 mmol) and 3,6-dichloropyridazine (0.772 g, 5.18 mmol) in 60 mL of butan-1-ol was heated at 135° C. in a sealed tube for 16 h. The solvent was removed in vacuo, and the residue was purified by flash chromatography to afford 842 mg of the title compound as a gray solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.96 (dd, 1H), 8.26 (d, 1H), 7.60-7.66 (m, 2H), 7.45 (d, 1H), 4.81 (s, 2H). LCMS (method A): [MH]+=332, tR=4.88 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6eed86e5d8b34c10825216c3cc78739a
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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