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

HRID 870698Notes

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

Participants

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

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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