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Potassium Carbonate → [3-(4-Aminomethyl-phenyl)-7-methyl-imidazo[1,2-b]pyridazin-6-yl]-butyl-amine

HRID 870698
Notes
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Reaction equation

HRID 870698 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:9]([CH3:11])=[CH:10][C:5]2=[N:4][CH:3]=1.Cl.[NH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O.CC#N.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[N:6]3[N:7]=[C:8]([NH:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:9]([CH3:11])=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343114-(Aminomethyl)benzeneboronic acid hydrochlorideHCID 86696400(3-Bromo-7-methyl-imidazo[1,2-b]pyridazin-6-yl)-butyl-amine

Product 1

HCID 86696399[3-(4-Aminomethyl-phenyl)-7-methyl-imidazo[1,2-b]pyridazin-6-yl]-butyl-amine

Reagents, catalysts & solvents 3

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 6342AcetonitrileSolvent
HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
150 °C

Procedure

A mixture of (3-bromo-7-methyl-imidazo[1,2-b]pyridazin-6-yl)-butyl-amine (115 mg, 0.41 mmol), (4-aminomethylphenyl)boronic acid hydrochloride (99.9 mg, 0.53 mmol), K2CO3 (170 mg, 1.23 mmol) and dichlorobis(triphenylphosphine)palladium(II) (14.4 mg, 0.021 mmol) in MeCN/water (3.2 ml/0.8 ml) was heated in a microwave at 150° C. for 15 min. The reaction mixture was diluted with MeCN and filtered. The filtrate was subjected to preparative HPLC to give the titled compound as AcOH salt (66.5 mg). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.01 (t, J=7.39 Hz, 3H) 1.42-1.52 (m, 2H) 1.73 (t, J=7.28 Hz, 2H) 2.23 (s, 3H) 3.41 (t, J=7.28 Hz, 2H) 4.16 (s, 2H) 7.44 (s, 1H) 7.52 (d, J=8.38 Hz, 2H) 7.75 (s, 1H) 8.25 (d, J=8.38 Hz, 2H) 8.54 (s, 1H). LRMS (ESI) m/z 310.2 [(M+H)]+, calc'd for C18H23N5: 309.42.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-c36572519994400e9f3edd86eed7e1e9
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08969565B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes