N1-(6-chloroimidazo[1,2-b]pyridazin-8-yl)benzene-1,4-diamine → HCID 178507709, compound

HRID 2239849Notes

Reaction equation

HRID 2239849 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.[NH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]1>O>[NH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:2]2[CH:3]=[C:4]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][CH:13]=3)[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[N:7]=2)[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 86611734N1-(6-chloroimidazo[1,2-b]pyridazin-8-yl)benzene-1,4-diamineHCID 178511674HCID 178511674, compound

Product 1

HCID 178507709HCID 178507709, compoundYield 154%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To N1-(6-chloroimidazo[1,2-b]pyridazin-8-yl)benzene-1,4-diamine (0.2 g, 0.77 mmol) from 1a was added trans-1,4-diaminocyclohexane (1.7 g, 15.0 mmol). The mixture was allowed to melt at 160° C. for 3 days. The melt was then cooled, diluted with water and extracted with dichloromethane. The organic layer was then concentrated in vacuo to give 0.4 g of crude N6-(trans-4-aminocyclohexyl)-N8-(4-aminophenyl)imidazo[1,2-b]pyridazine-6,8-diamine.

Workup

  1. temperatureThe melt was then cooled
  2. extractionextracted with dichloromethane
  3. concentrationThe organic layer was then concentrated in vacuo

Sources & evidence

ORD record
ord-053eba1c98d54a539d863e5c0eb6f505
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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