P-Phenylenediamine → N1-(6-chloroimidazo[1,2-b]pyridazin-8-yl)benzene-1,4-diamine

HRID 2239848Notes

Reaction equation

[NH2:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.Br[C:18]1[C:19]2[N:20]([CH:25]=[CH:26][N:27]=2)[N:21]=[C:22]([Cl:24])[CH:23]=1>CCO>[Cl:24][C:22]1[CH:23]=[C:18]([NH:1][C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)[C:19]2[N:20]([CH:25]=[CH:26][N:27]=2)[N:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

p-Aminoaniline (0.48 g, 4.4 mmol) and triethylamine (1.3 ml, 9.2 mmol) were added to 8-bromo-6-chloroimidazo[1,2-b]pyridazine HCl (1.0 g, 4.2 mmol) from Example I(1), step 1b in EtOH (20 mL). The mixture was heated to 90° C. and stirred for 1 hr. The solution was then concentrated in vacuo to give crude N1-(6-chloroimidazo[1,2-b]pyridazin-8-yl)benzene-1,4-diamine. Cold ethanol was then added and the crude solid rinsed 3×. Following filtration, collected 0.45 g of the desired material.

Workup

concentrationThe solution was then concentrated in vacuo

Sources & evidence

ORD record: ord-020c3d48085a4c1994de963268a52423
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723336B2

Reaction notes

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