3-Methylbenzoic acid → N-[3-(imidazo[1,2-b]pyridazin-6-ylethynyl)phenyl]-3-methylbenzamide

HRID 589913Notes

Reaction equation

[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([C:10]#[C:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15])=[N:5]2.[C:19]1([CH3:28])[CH:24]=[CH:23][CH:22]=[C:21]([C:25](O)=[O:26])[CH:20]=1.Cl.CN(C)CCCN=C=NCC.CO.C(Cl)Cl>ClC(Cl)C.CN(C)C1C=CN=CC=1>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([C:10]#[C:11][C:12]1[CH:13]=[C:14]([NH:15][C:25](=[O:26])[C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([CH3:28])[CH:20]=3)[CH:16]=[CH:17][CH:18]=1)=[N:5]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 3-(imidazo[1,2-b]pyridazin-6-ylethynyl)aniline (93.6 mg, 0.4 mmol, 1 eq) and m-toluic acid (55 mg, 1 eq) in anhydrous dichloroethane (4 mL) under nitrogen atmosphere was added 4-(dimethylamino)pyridine (10 mg, 0.2 eq) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (92.2 mg, 1.2 eq). After the reaction was stirred at 60° C. for four hours and was cooled to room temperature, white precipitates were observed. It was filtered directly to give a white solid. This solid was further subject to a gradient column chromatography (MeOH-DCM 1:50 to 1:20) to yield N-[3-(imidazo[1,2-b]pyridazin-6-ylethynyl)phenyl]-3-methylbenzamide as a white solid in amount of 85 mg.

Workup

temperaturewas cooled to room temperature
customwhite precipitates
filtrationIt was filtered directly
customto give a white solid

Sources & evidence

ORD record: ord-e8bf2536826146638569fcc5aa729760
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233968B1

Reaction notes

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