Butylamine → 3-Bromo-6-(butylamino)imidazo[1,2-b]pyridazine

HRID 870625Notes

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

Participants

Reactant 2

HCID 8007Butylamine

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

Product 1

HCID 866963223-Bromo-6-(butylamino)imidazo[1,2-b]pyridazineYield 63%

Procedure

A solution of 3-bromo-6-chloroimidazo[1,2-b]pyridazine (1.2 g, 5.2 mmol) and N-butylamine (2 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-butylimidazo[1,2-b]pyridazin-6-amine (887 mg, 63% yield) as a white solid: 1H NMR (METHANOL-d4) δ: 7.53 (d, J=9.6 Hz, 1H), 7.39 (s, 1H), 6.69 (d, J=9.9 Hz, 1H), 3.38 (t, J=7.1 Hz, 2H), 1.59-1.73 (m, 2H), 1.41-1.53 (m, 2H), 1.01 (t, J=7.3 Hz, 3H); LRMS (ESI) m/e 269.1 [(M+H)+, calcd for C10H14BrN4 269.0].

Workup

custompurified by preparative HPLC (neutral)

Sources & evidence

ORD record: ord-8448c9a029ca4e72a35ac0dd31b11632
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969565B2

Reaction notes

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