1-(3-Aminopropyl)-2-pyrrolidinone → 1-(3-(3-Bromoimidazo[1,2-b]pyridazin-6-ylamino)propyl)pyrrolidin-2-one

HRID 1162119Notes

Reaction equation

HRID 1162119 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.[NH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[O:21].C(Cl)Cl.CO.[NH4+].[OH-]>>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:20][CH2:19][CH2:18][C:17]3=[O:21])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 821111-(3-Aminopropyl)-2-pyrrolidinoneHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 686481591-(3-(3-Bromoimidazo[1,2-b]pyridazin-6-ylamino)propyl)pyrrolidin-2-one

Procedure

Prepared from 3-bromo-6-chloroimidazo[1,2-b]pyridazine and 1-(3-aminopropyl)pyrrolidin-2-one according to general procedure 1 providing the intermediate (150 mg, 58%) as a white solid; Rf=0.58 (CH2Cl2/MeOH/NH4OH, 160:18:2); 1H NMR (500 MHz, CD3OD) δ 7.55 (d, J=9.7 Hz, 1H), 7.39 (s, 1H), 6.68 (d, J=9.7 Hz, 1H), 3.53 (t, J=7.1 Hz, 2H), 3.43-3.38 (m, 4H), 2.39 (t, J=8.0 Hz, 2H), 2.08 (quin, J=7.6 Hz, 2H), 1.94 (quin, J=6.9 Hz, 2H); ES-MS: (M+H)=338, 340 m/z.

Sources & evidence

ORD record
ord-76ae5f4c16c24473a980529a11538828
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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