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

HRID 589913
Notes
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Reaction equation

HRID 589913 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 74183-Methylbenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21226129Dichloromethane methanolHCID 1186384153-(Imidazo[1,2-b]pyridazin-6-ylethynyl)aniline

Product 1

HCID 118638413N-[3-(imidazo[1,2-b]pyridazin-6-ylethynyl)phenyl]-3-methylbenzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

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

  1. temperaturewas cooled to room temperature
  2. customwhite precipitates
  3. filtrationIt was filtered directly
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes