4-Aminobenzonitrile → HCID 86618520, compound

HRID 2239879Notes

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.[C:12]([C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)#[N:13].[CH3:21]C([O-])(C)C.[K+]>C1COCC1>[Cl:8][C:6]1[C:7]([CH3:21])=[C:2]([NH:18][C:17]2[CH:19]=[CH:20][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)[C:3]2[N:4]([CH:9]=[CH:10][N:11]=2)[N:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of free based 8-bromo-6-chloroimidazo[1,2-b]pyridazine from Example 1, step 1b (100 mg, 0.35 mmol) in THF (1.0 ml) was added p-cyanoaniline (42 mg, 0.35 mmol) and a 1.0 M solution of KOt-Bu in THF (3.0 eq, 1.05 ml, 1.05 mmol). The mixture was allowed to heat at 50° C. for 1 hour. The solution was then concentrated in vacuo to dryness to provide 4-(6-chloro-7-methylimidazo[1,2-b]pyridazin-8-ylamino)benzonitrile as a solid m/e 284 (MH+)

Workup

additionTo a mixture
concentrationThe solution was then concentrated in vacuo to dryness

Sources & evidence

ORD record: ord-f0c3da1e1f964fd9a057d7e9086558ca
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723336B2

Reaction notes

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