p-Toluenesulfonic acid → HCID 178521579, compound

HRID 2205216Notes

Reaction equation

HRID 2205216 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([Br:11])=[CH:9][N:10]=2)[N:7]=1.CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]1>CS(C)=O>[Br:11][C:8]1[N:6]2[N:7]=[C:2]([NH:23][C@H:24]3[CH2:29][CH2:28][C@H:27]([OH:30])[CH2:26][CH2:25]3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 178511715HCID 178511715, compound

Product 1

HCID 178521579HCID 178521579, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To 6-chloro-3-bromoimidazo[1,2-b]pyridazine (1.00 g, 4.30 mmol, 1.0 equiv) and p-TSA (818 mg, 4.30 mmol, 1.0 equiv) in DMSO (7.00 mL) was added trans-4-aminocyclohexanol (1.49 g, 12.9 mmol, 3.0 equiv). The mixture was heated at 100° C. for 24 h. Purification by column chromatography using 5% methanol in dichloromethane elution gave 1.1 g of the yellow solid, 83%.

Workup

  1. customPurification by column chromatography
  2. wash5% methanol in dichloromethane elution

Sources & evidence

ORD record
ord-7489922e129a48c7aa8c42cee6484a13
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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