Hydrochloric Acid → N,N-dimethyl-N'-(6-n-propyl-2-trifluoromethylimidazo[1,2-b]pyridazin-3-ylsulfonyl)formamidine

HRID 969723Notes

Reaction equation

HRID 969723 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([S:15]([N:18]=[CH:19][N:20]([CH3:22])[CH3:21])(=[O:17])=[O:16])=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=2)[N:7]=1.[Br-].[CH2:24]([Zn+])[CH2:25][CH3:26].O.Cl>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:21][N:20]([CH3:22])[CH:19]=[N:18][S:15]([C:8]1[N:6]2[N:7]=[C:2]([CH2:24][CH2:25][CH3:26])[CH:3]=[CH:4][C:5]2=[N:10][C:9]=1[C:11]([F:14])([F:13])[F:12])(=[O:17])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 74015820HCID 74015820, compoundHCID 178455869HCID 178455869, compound

Product 1

HCID 68536680N,N-dimethyl-N'-(6-n-propyl-2-trifluoromethylimidazo[1,2-b]pyridazin-3-ylsulfonyl)formamidine

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of N′-(6-chloro-2-trifluoromethylimidazo[1,2-b]pyridazin-3-ylsulfonyl)-N,N-dimethylformamidine (1.00 g, 2.81 mmol) and [1,3-bis(diphenylphosphino)propane]nickel(II) dichloride (0.076 g, 0.14 mmol) in tetrahydrofuran (8.0 ml) was added dropwise a solution of n-propylzinc bromide in tetrahydrofuran (0.5 M, 8.43 ml, 4.22 mmol) with stirring under ice-cooling and nitrogen stream. The reaction mixture was stirred for 30 minutes under ice-cooling and 4.5 hours at room temperature, then poured into cold water and made acid with dilute hydrochloric acid. The precipitated solid was collected by filtration, washed with dilute hydrochloric acid, then water, and purified by silica gel column chromatography (ethyl acetate:chloroform=2:5) to give the title compound as white crystals. The yield was 0.62 g (60.7%).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred for 30 minutes under ice-
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with dilute hydrochloric acid
  5. customwater, and purified by silica gel column chromatography (ethyl acetate:chloroform=2:5)

Sources & evidence

ORD record
ord-47dc2caa5c5a40d288b9c1333f8cb7cf
Source dataset
uspto-grants-2007_12
Patent number
US07307165B2

Reaction notes

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