p-Toluenesulfonic acid → HCID 90388249, compound

HRID 2205203Notes

Reaction equation

HRID 2205203 reaction equation
Br[C:2]1[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>CS(C)=O>[Cl:8][C:6]1[CH:7]=[C:2]([NH:26][CH:23]2[CH2:25][CH2:24]2)[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 69828CyclopropylamineHCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 90388249HCID 90388249, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 8-bromo-6-chloroimidazo[1,2-b]pyridazine (1.00 g, 3.21 mmol, 1.0 equiv) and p-TSA (611 mg, 3.21 mmol, 1.0 equiv) in DMSO (10.0 mL) was added cyclopropylamine (1.13 mL, 16.1 mmol, 5.0 equiv) and heated to 100° C. for 24 h. Purification by column chromatography using 50% ethyl acetate in hexanes elution gave 536 mg of the white solid, 80%.

Workup

  1. customPurification by column chromatography
  2. wash50% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-244af766cb9b4ccc966b39a58823707d
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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