4-Toluenesulfonyl chloride → HCID 86665020, compound

HRID 1051760Notes

Reaction equation

HRID 1051760 reaction equation
Cl.[N:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9]([OH:11])=[CH:8][CH:7]=[N:6]2.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(Cl)Cl>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:11][C:9]2[C:10]3[N:5]([CH:4]=[CH:3][N:2]=3)[N:6]=[CH:7][CH:8]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178479634HCID 178479634, compound

Product 1

HCID 86665020HCID 86665020, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of imidazo[1,2-b]pyridazin-8-ol hydrochloride (D-5) (4 g, 23.3 mmol, 1.0 eq) and triethylamine (7.1 g, 70.0 mmol, 3.0 eq) in DCM (50 mL), 4-toluenesulfonyl chloride (5.3 g, 28.0 mmol, 1.2 eq) is added in portions and the resulting mixture is stirred at RT for 1 h. The mixture is washed with brine, dried over Na2SO4 and filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography on silica gel (10-50% ethyl acetate-petro ether) to afford the product, imidazo[1,2-b]pyridazin-8-yl 4-methylbenzenesulfonate (D-6).

Workup

  1. washThe mixture is washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is purified by flash column chromatography on silica gel (10-50% ethyl acetate-petro ether)

Sources & evidence

ORD record
ord-5e8fc90fa7ac4ff5b256052e612279bf
Source dataset
uspto-grants-2016_07
Patent number
US09388183B2

Reaction notes

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