N,N-Diethylethylenediamine → N1-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)-N2,N2-diethylethane-1,2-diamine

HRID 1162127Notes

Reaction equation

HRID 1162127 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]([N:14]([CH2:18][CH3:19])[CH2:15][CH2:16][NH2:17])[CH3:13].C(Cl)Cl.CO.[NH4+].[OH-]>>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:17][CH2:16][CH2:15][N:14]([CH2:18][CH3:19])[CH2:12][CH3:13])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 68648436N1-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)-N2,N2-diethylethane-1,2-diamine

Procedure

Prepared from 3-bromo-6-chloroimidazo[1,2-b]pyridazine and N1,N1-diethylethane-1,2-diamine according to general procedure 1 providing the intermediate (160 mg, 80%) as a clear oil: Rf=0.22 (CH2Cl2/MeOH/NH4OH, 160:18:2); 1H NMR (500 MHz, CD3OD) δ 7.55 (d, J=9.7 Hz, 1H), 7.40 (s, 1H), 6.68 (d, J=9.7 Hz, 1H), 3.52 (t, J=6.0 Hz, 2H), 2.79 (t, J=5.8 Hz, 2H), 2.68 (quart, J=7.2 Hz, 4H), 1.12 (t, J=7.2 Hz, 6H); ES-MS: (M+H)=312, 314 m/z.

Sources & evidence

ORD record
ord-f85376af62674777825506e94735fb7c
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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