6-Amino-3-chloropyridazine → 3-Pyridazinamine, 6-(4-methyl-1-piperazinyl)-

HRID 1919167Notes

Reaction equation

Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:2]2[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=2)[CH2:12][CH2:11]1

Participants

Reactant 2

HCID 216436-Amino-3-chloropyridazine

HCID 531671-Methylpiperazine

Product 1

HCID 203168163-Pyridazinamine, 6-(4-methyl-1-piperazinyl)-Yield 78%

Conditions

Temperature: 170 °C

Procedure

A sealed tube equipped with a magnetic stirrer was charged with 6-chloro-pyridazin-3-amine (1.3 g, 10 mmol) and 1-methylpiperazine (15 mL). The reaction mixture was heated at 170° C. for 3 h. It was then cooled to room temperature and concentrated under reduced pressure. The resulting residue was washed with CH3CN (20 mL) to afford 342a as a yellow solid (1.5 g, 78%). MS: [M+H]+ 194. 1H NMR (500 MHz, DMSO) δ 7.12 (d, J=9.0 Hz, 1H), 6.74 (d, J=9.0 Hz, 1H), 5.72 (s, 2H), 3.27 (t, J=4.5 Hz, 4H), 2.40 (t, J=4.5 Hz, 4H), 2.20 (s, 3H).

Workup

customA sealed tube equipped with a magnetic stirrer
temperatureIt was then cooled to room temperature
concentrationconcentrated under reduced pressure
washThe resulting residue was washed with CH3CN (20 mL)

Sources & evidence

ORD record: ord-b6daf58085734127b9ea8d40dbb5e2e0
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618107B2

Reaction notes

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