Water → HCID 22640035, compound

HRID 2415094Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

0.18 g (3.6 mmol) of 6-chloro-3-nitro-imidazo[1,2-b]pyridazine are added to a solution of 0.85 g (3.6 mmol) of 4-[(5-chloro-pyrimidin-4-ylamino)-methyl]-phenol (from example A14) and 2.5 g (18 mmol) of potassium carbonate in 10 ml of dry N,N-dimethylformamide and the reaction mixture is stirred at 80° C. for 3 h. The temperature is allowed to raise to room temperature and the mixture is poured into water (100 ml). The precipitate is filtered off and purified by silica gel chromatography (toluene/dioxane=2:1) to yield 1.1 g (78%) of the title compound as a beige powder of m.p. 185° C.

Workup

temperatureto raise to room temperature
filtrationThe precipitate is filtered off
custompurified by silica gel chromatography (toluene/dioxane=2:1)

Sources & evidence

ORD record: ord-1301dd36784b40ceaf44e23eb0e50157
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818642B2

Reaction notes

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