N-(3-Aminopropyl)morpholine → 3-Bromo-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine

HRID 1162104Notes

Reaction equation

HRID 1162104 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.[O:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][NH2:21])[CH2:14][CH2:13]1.C(Cl)Cl.CO.[NH4+].[OH-]>>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:21][CH2:20][CH2:19][CH2:18][N:15]3[CH2:16][CH2:17][O:12][CH2:13][CH2:14]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 61055N-(3-Aminopropyl)morpholineHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 686478363-Bromo-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine

Procedure

Prepared from 3-bromo-6-chloroimidazo[1,2-b]pyridazine and 3-morpholinopropylamine according to general procedure 1 providing the amino compound (1.30 g, 59%) as an orange oil; Rf=0.66 (CH2Cl2/MeOH/NH4OH, 160:18:2); 1H NMR (500 MHz, CD3OD) δ 7.54 (d, J=9.7 Hz, 1H), 7.39 (s, 1H), 6.47 (d, J=9.7 Hz, 1H), 3.71-3.69 (m, 4H), 3.42 (t, J=6.9 Hz, 2H), 2.51-2.48 (m, 6H), 1.92-1.89 (m, 2H); ES-MS: (M+H)=340, 342 m/z.

Sources & evidence

ORD record
ord-8ef0c7c932aa4e12b9095d364ceed325
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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