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

HRID 456107Notes

Reaction equation

HRID 456107 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 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 B): [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-e29c0360f1314d3aa3f22f69bf5b83a8
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

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