2-Methoxyethylamine → 3-bromo-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine

HRID 870622Notes

Reaction equation

[Br:1][C:2]1[N:6]2[N:7]=[C:8](Cl)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][NH2:16]>>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:16][CH2:15][CH2:14][O:13][CH3:12])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 574706223-bromo-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amineYield 62%

Procedure

A solution of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (844 mg, 3.77 mmol) and 2-methoxyethanamine (1.44 mL) was heated at 170° C. (microwave) for 30 min. The resulting mixture was cooled to room temperature and purified by preparative HPLC (neutral) to afford 3-bromo-N-(2-methoxyethyl)imidazo[1,2-b]pyridazin-6-amine (630 mg, 62% yield) as a off-white solid: 1H NMR (METHANOL-d4) δ: 7.56 (d, J=9.9 Hz, 1H), 7.41 (s, 1H), 6.74 (d, J=9.6 Hz, 1H), 3.62-3.76 (m, 2H), 3.50-3.62 (m, 2H), 3.42 (s, 3H); LRMS (ESI) m/e 271.1 [(M+H)+, calcd for C9H12BrN4O 271.0]

Workup

custompurified by preparative HPLC (neutral)

Sources & evidence

ORD record: ord-59f3c5136af946199e13995e9d29d700
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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