N-(6-Chloroimidazo[1,2-b]pyridazin-8-yl)benzenesulfonamide → HCID 178511643, compound

HRID 2239868Notes

Reaction equation

HRID 2239868 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[NH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([NH2:28])[CH2:24][CH2:23]1>O>[NH2:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([NH:28][C:2]2[CH:3]=[C:4]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 86611749N-(6-Chloroimidazo[1,2-b]pyridazin-8-yl)benzenesulfonamideHCID 178511674HCID 178511674, compound

Product 1

HCID 178511643HCID 178511643, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N-(6-chloroimidazo[1,2-b]pyridazin-8-yl)benzenesulfonamide (100 mg, 0.325 mmol) from 1a was added trans-1,4-diaminocyclohexane (1000 mg, 8.77 mmol). The mixture was allowed to melt at 165° C. for 3 days. The melt was then cooled, water was added followed by extraction with dichloromethane. The organic layer was then concentrated in vacuo and purified by preparative HPLC. This gave 4.5 mg (2%) of the title compound as a TFA salt. 1H NMR (500 MHz, MeOH-D3) δ ppm 7.97 (2H, d, J=5 Hz), 7.85 (1H, s), 7.71 (1H, s), 7.63 (1H, m), 7.56 (2H, m), 6.63 (1H, s), 3.64 (1H, m), 3.12 (1H, m), 2.23-2.04 (4H, m), 1.51 (2H, m), 1.34 (2H, m). LC/MS m/e 387 (MH+). HPLC, 1.60 min. Waters Sunfire C18 4.6×50. 0%-100% B. B: 90% MeOH, 10% H2O, 0.1% TFA. A: 10% MeOH, 90% H2O, 0.1% TFA.

Workup

  1. temperatureThe melt was then cooled
  2. extractionfollowed by extraction with dichloromethane
  3. concentrationThe organic layer was then concentrated in vacuo
  4. custompurified by preparative HPLC
  5. customHPLC, 1.60 min

Sources & evidence

ORD record
ord-1dee47a21e244e59bdc3fd6d90677f86
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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