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

HRID 1162109Notes

Reaction equation

HRID 1162109 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.[NH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.Cl>CCOCC>[ClH:1].[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][NH:13][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

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 195092-PyridinemethanamineHCID 57352521(6-Chloroimidazo(1,2-b)pyridazin-3-yl)methanol

Product 1

HCID 68648784(6-(Pyridin-2-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl)methanol hydrochlorideYield 20%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from (6-chloroimidazo[1,2-b]pyridazin-3-yl)methanol (7) and 2-(aminomethyl)pyridine 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 (48 mg, 20%) as a yellow solid; 1H NMR (300 MHz, CD3OD) δ 8.49 (d, J=4.2 Hz, 1H), 7.77 (dt, J=1.7, 9.4 Hz, 1H), 7.61-7.52 (m, 2H), 7.35 (s, 1H), 7.31-7.26 (m, 1H), 6.77 (d, J=9.7 Hz, 1H), 4.74 (s, 2H), 4.67 (s, 2H); 13C NMR (75 MHz, CD3OD) δ 160.2, 154.9, 149.6, 138.8, 137.8, 129.8, 129.5, 125.9, 123.7, 123.6, 114.2, 53.8, 47.6; HPLC tR=7.0 min (Synergi), 96.1%; ES-MS: (M+H)=256 m/z.

Sources & evidence

ORD record
ord-d1144805fde5415db61af124b2066bfa
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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