tert-Butyl (3-aminopropyl)carbamate → tert-Butyl 3-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)propylcarbamate

HRID 1162143Notes

Reaction equation

HRID 1162143 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][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].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][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 3

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 57470631tert-Butyl 3-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)propylcarbamate

Procedure

Prepared from 3-bromo-6-chloroimidazo[1,2-b]pyridazine and tert-butyl 3-aminopropylcarbamate according to general procedure 1 providing the intermediate (300 mg, 63%) as a yellow oil: Rf=0.65 (CH2Cl2/MeOH/NH4OH, 160:18:2); 1H NMR (500 MHz, CDCl3) δ 7.56 (d, J=9.6 Hz, 1H), 7.46 (s, 1H), 6.46 (d, J=9.6 Hz, 1H), 5.13-5.10 (m, 2H), 3.53 (quart, J=6.2 Hz, 2H), 3.27-3.23 (m, 2H), 1.84-1.79 (m, 2H), 1.46 (s, 9H); ES-MS: (M+H)=370, 372 m/z.

Sources & evidence

ORD record
ord-49e757cae2ba43edbb1823abc98907ec
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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