Hydrochloric Acid → 3-Chloro-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine hydrochloride

HRID 1162103Notes

Reaction equation

HRID 1162103 reaction equation
[Cl: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.Cl>CCOCC>[ClH:1].[Cl: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

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 61055N-(3-Aminopropyl)morpholineHCID 152710143,6-Dichloroimidazo[1,2-b]pyridazine

Product 1

HCID 686482743-Chloro-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine hydrochlorideYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from 3,6-dichloroimidazo[1,2-b]pyridazine and 3-morpholinopropylamine according to general procedure 3. The free base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (153 mg, 57%) as a white solid; 1H NMR (500 MHz, CD3OD) δ 7.60 (d, J=9.7 Hz, 1H), 7.39 (s, 1H), 6.70 (d, J=9.7 Hz, 1H), 3.90 (br, 4H), 3.53 (t, J=6.7 Hz, 2H), 3.35-3.27 (m, 6H), 2.20-2.14 (m, 2H): 13C NMR (75 MHz, CD3OD) δ 155.8, 137.2, 127.9, 126.1, 115.6, 114.7, 65.2, 56.8, 53.4, 39.6, 24.5; HPLC tR=8.9 min (Synergi), >99%; ES-MS: (M+H)=332 m/z.

Sources & evidence

ORD record
ord-6e4cf192c2e44b848ec9991e601980c9
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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