Methanol → 6-Chloro-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carboxamide

HRID 2239872Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]2[N:6]([C:8]([C:11]#[N:12])=[CH:9][N:10]=2)[N:7]=1.[OH-:29].[Na+].CO>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]([CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:5]2[N:6]([C:8]([C:11]([NH2:12])=[O:29])=[CH:9][N:10]=2)[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-chloro-3-cyano-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine (25 mgs) from Example XXXI(1) step 1b, 6N NaOH (0.1 mL), MeOH (0.1 mL) and dioxane (1 mL) in a vial was heated to 100° C. for 16 h. The mixture was cooled to room temperature and concentrated in vacuo. Upon addition of 1M HCl a precipitate forms. The precipitate was collected by filtration and dried to provide 35 mgs of crude 6-chloro-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carboxamide.

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated in vacuo
additionUpon addition of 1M HCl a precipitate forms
filtrationThe precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-e46b970cc71c4a5db8625b0624b31c97
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723336B2

Reaction notes

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