Sodium Chloride → (4-Chloro-2-fluorophenyl)(6-chloro-2-methylimidazo[1,2-b]pyridazin-3-yl)methanone

HRID 597856Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[N:6][C:5](/[N:8]=[C:9](/N(C)C)\[CH3:10])=[CH:4][CH:3]=1.Cl[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[F:25])=[O:17].[Cl-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CC(=O)OCC.O.CN(C)C=O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:16]([C:15]2[N:6]3[N:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]3=[N:8][C:9]=2[CH3:10])=[O:17])=[C:19]([F:25])[CH:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In a round bottom flask combine (E)-N′-(6-chloropyridazin-3-yl)-N,N-dimethylacetimidamide (36.61 g, 184.3 mmol), 2-chloro-1-(4-chloro-2-fluorophenyl)ethanone (38.15 g, 1 equiv.), and dimethylformamide (150 mL). Place under nitrogen then heat at 120° C. for 4 h. Let cool to RT and stir overnight. Dilute with EA (1 L) and water (500 mL). Extract organics three times with water followed by aqueous saturated sodium chloride aqueous. Dry organics over anhydrous magnesium sulfate. Filter and concentrate in vacuo. Purify by silica plug (hexane→4:1 hexane:EA→3:1 hexane:EA→2:1 hexane:EA→1:1 hexane:EA) and isolate the title compound (33.8 g, 57%) as a light green solid. LCMS (4 min=324.0, 326.0, M+1).

Workup

customIn a round bottom flask combine
temperatureLet cool to RT
filtrationFilter
concentrationconcentrate in vacuo
customPurify by silica plug (hexane→4:1 hexane

Sources & evidence

ORD record: ord-8a133918b155450c86a4f24fad571d22
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897600B2

Reaction notes

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