3,6-Dichloropyridazine → 6-(1-{6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl}ethyl)-5,7-difluoroquinoline

HRID 1892399Notes

Reaction equation

HRID 1892399 reaction equation
[F:1][C:2]1[C:11]([CH:12]([CH3:17])[C:13]([NH:15][NH2:16])=O)=[C:10]([F:18])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl:19][C:20]1[N:21]=[N:22][C:23](Cl)=[CH:24][CH:25]=1>C(O)CCC>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]2[N:15]([C:13]([CH:12]([C:11]3[C:2]([F:1])=[C:3]4[C:8](=[CH:9][C:10]=3[F:18])[N:7]=[CH:6][CH:5]=[CH:4]4)[CH3:17])=[N:21][N:22]=2)[N:16]=1

Participants

4

Reactant 2

HCID 673313,6-DichloropyridazineHCID 669271092-(5,7-Difluoro-quinolin-6-yl)-propionic acid hydrazide

Product 1

HCID 581905406-(1-{6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl}ethyl)-5,7-difluoroquinoline

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2-(5,7-difluoro-quinolin-6-yl)-propionic acid hydrazide (2.404 g, 9.404 mmol) and 3,6-dichloropyridazine (2.138 g, 14.35 mmol) in butan-1-ol (60 mL) was stirred at 135° C. in a sealed tube overnight. Solvent was removed under reduced pressure, and the residue was purified by column chromatography to afford 1.476 g (45% for two steps) of the title compound as a pale yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.93 (dd, 1H), 8.36 (dd, 1H), 8.07 (d, 1H), 7.62 (dd, 1H), 7.43 (dd, 1H), 7.05 (d, 1H), 5.26 (q, 1H), 2.13 (d, 1H). LCMS (method A): [MH]+=346, tR=5.00 min.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-506df3c07873499f9b25a51f864bf63c
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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