Potassium Fluoride → 4-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexane-1-sulfonamide

HRID 1483838Notes

Reaction equation

HRID 1483838 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([S:8]([NH2:11])(=[O:10])=[O:9])[CH2:4][CH2:3]1.Cl[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)=[CH:20][N:21]=2)[N:18]=1.[F-].[K+]>CS(C)=O.[Cl-].[Na+].O>[Cl:28][C:24]1[CH:23]=[C:22]([C:19]2[N:17]3[N:18]=[C:13]([NH:1][CH:2]4[CH2:7][CH2:6][CH:5]([S:8]([NH2:11])(=[O:9])=[O:10])[CH2:4][CH2:3]4)[CH:14]=[CH:15][C:16]3=[N:21][CH:20]=2)[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 522689Potassium FluorideHCID 574186866-Chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazineHCID 893898974-Aminocyclohexane-1-sulfonamide

Product 1

HCID 712353004-((3-(3-Chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)amino)cyclohexane-1-sulfonamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-aminocyclohexane-1-sulfonamide (200 mg, 1.12 mmol), 6-chloro-3-(3-chlorophenyl)imidazo[1,2-b]pyridazine (200 mg, 0.76 mmol) and KF (500 mg, 8.6 mmol) in DMSO (2 mL) was heated at 120° C. overnight. LCMS showed the reaction was complete. The mixture was poured into brine (80 mL) and extracted with EtOAc (30 mL×3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by to prep. HPLC give two isomers: EX. 8-81 isomer 1 (7.0 mg) and EX. 8-81 isomer 2 (8.1 mg) as white solid.

Workup

  1. extractionextracted with EtOAc (30 mL×3)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by
  6. customHPLC give two isomers

Sources & evidence

ORD record
ord-3cd0fb73d6e44b369387cef95200a08f
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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