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

HRID 1959648Notes

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 at 130° C. for 12 h. The solvent was removed under reduced pressure. The crude was partitioned in aqueous solution of K2CO3 and EtOAc. The organic layers were combined and concentrated to give a solid, which was purified by silica gel column to give the title compound as black solid (190 mg, 53%). 1H-NMR (400 MHz, DMSO-d6) 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 under reduced pressure
customThe crude was partitioned in aqueous solution of K2CO3 and EtOAc
concentrationconcentrated
customto give a solid, which
customwas purified by silica gel column

Sources & evidence

ORD record: ord-e624f91a227f423bb8afeb52b51bc604
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410264B2

Reaction notes

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