3,6-Dichloropyridazine → 6-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)difluoromethyl)quinoline

HRID 456062Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[F:9][C:10]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:11]([NH:13][NH2:14])=O>CCCCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:4]([C:11]([C:10]([F:25])([F:9])[C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]=[CH:20][CH:19]=[CH:18]4)=[N:13][N:14]=2)[N:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

3,6-dichloropyridazine (160 mg, 1.07 mmol) and difluoro-quinolin-6-yl-acetic acid hydrazide (254 mg, 1.07 mmol) were added in n-BuOH (20 mL). The reaction mixture was heated to 130° C. for 12 hours. The solvent was removed by vacuo. The crude was extracted by the solution of K2CO3 and EtOAc. The organic layer was collected and concentrated to give a solid, which was purified by silica gel column to give 6-[(6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)-difluoro-methyl]-quinoline as a black solid (190 mg, 53%). 1H-NMR (DMSO) δ ppm 7.62 (m, 2H); 7.90 (m, 1H); 8.22 (m, 1H); 8.35 (m, 1H); 8.65 (m, 2H); 9.02 (m, 1H).

Workup

customThe solvent was removed by vacuo
extractionThe crude was extracted by the solution of K2CO3 and EtOAc
customThe organic layer was collected
concentrationconcentrated
customto give a solid, which
customwas purified by silica gel column

Sources & evidence

ORD record: ord-ce19703066fa4f49b919a5014d2c945b
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497368B2

Reaction notes

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