Ethyl Acetate → 6-[N-(5-Bromo-2-propoxybenzyl)-N-ethylamino]-3-cyanopyridazine

HRID 840316Notes

Reaction equation

Cl.[CH2:2]([NH:4][CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:7]=1[O:13][CH2:14][CH2:15][CH3:16])[CH3:3].Cl[C:18]1[N:19]=[N:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>CN1C(=O)CCC1>[Br:12][C:10]1[CH:9]=[CH:8][C:7]([O:13][CH2:14][CH2:15][CH3:16])=[C:6]([CH:11]=1)[CH2:5][N:4]([C:18]1[N:19]=[N:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 110 °C

Procedure

N-ethyl 2-propoxy-5-bromobenzylamine hydrochloride 2 (5.17 g, 16.8 mmol) and 3-chloro-6-cyanopyridazine (2.65 g, 16.8 mmol) were dissolved in NMP (25 ml) and sodium hydrogen carbonate added (3.54 g, 42.1 mmol). The mixture was heated at 110 ° C. under argon for 7.5 hours and then allowed to cool to ambient temperature. The mixture was poured into ethyl acetate (200 ml) washed with water (5×200 ml) and brine (200 ml), the organic phase dried over MgSO4 and concentrated in vacuo. The residue was purified by MPLC (20% ethyl acetate/hexane) and then crystallised from ether/hexane to give the title product (4.80 g, 76%).

Workup

temperatureto cool to ambient temperature
washwashed with water (5×200 ml) and brine (200 ml)
dry with materialthe organic phase dried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by MPLC (20% ethyl acetate/hexane)
customcrystallised from ether/hexane

Sources & evidence

ORD record: ord-0c82b1ea71ee47e8bb09ca1391ec1fa8
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365603B1

Reaction notes

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