Hydrochloric Acid → (6-(3-Morpholinopropylamino)imidazo[1,2-b]pyridazin-3-yl)methanol hydrochloride

HRID 1162108Notes

Reaction equation

HRID 1162108 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][OH:12])=[CH:9][N:10]=2)[N:7]=1.[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][NH2:22])[CH2:15][CH2:14]1.Cl>CCOCC>[ClH:1].[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][NH:22][C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([CH2:11][OH:12])=[CH:9][N:10]=3)[N:7]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 61055N-(3-Aminopropyl)morpholineHCID 57352521(6-Chloroimidazo(1,2-b)pyridazin-3-yl)methanol

Product 1

HCID 68648037(6-(3-Morpholinopropylamino)imidazo[1,2-b]pyridazin-3-yl)methanol hydrochlorideYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from (6-chloroimidazo[1,2-b]pyridazin-3-yl)methanol (7) and and 3-morpholinopropylamine according to general procedure 4 (StepB). The free base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (174 mg, 65%) as a yellow solid; 1H NMR (500 MHz, CD3OD) δ 7.58 (d, J=9.7 Hz, 1H), 7.63 (s, 1H), 6.98 (d, J=9.7 Hz, 1H), 4.89 (s, 2H), 3.93-3.91 (m, 4H), 3.55-3.52 (t, J=6.6 Hz, 2H), 3.34-3.25 (m, 6H), 2.22-2.16 (m, 2H); 13C NMR 75 MHz, CD3OD) δ 156.3, 135.7, 130.7, 124.7, 123.5, 118.0, 65.1, 56.7, 53.5, 53.3, 39.6, 24.3; HPLC tR=7.4 min (Synergi), 98.9%; ES-MS: (M+H)=292 m/z.

Sources & evidence

ORD record
ord-3b5dce7fc95d4f81b70774abdd01598e
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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