Hydrochloric Acid → (E)-N1,N1-Diethyl-N2-(3-(hex-1-enyl)imidazo[1,2-b]pyridazin-6-yl)ethane-1,2-diamine hydrochloride

HRID 1162128Notes

Reaction equation

HRID 1162128 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:19](/B(O)O)=[CH:20]\[CH2:21][CH2:22][CH2:23][CH3:24].[ClH:28]>CCOCC>[ClH:28].[CH2:15]([N:14]([CH2:17][CH3:18])[CH2:13][CH2:12][NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2](/[CH:19]=[CH:20]/[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:3][N:4]=2)[N:7]=1)[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 68648436N1-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)-N2,N2-diethylethane-1,2-diamine

Product 1

HCID 68648141(E)-N1,N1-Diethyl-N2-(3-(hex-1-enyl)imidazo[1,2-b]pyridazin-6-yl)ethane-1,2-diamine hydrochlorideYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2. The free-base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (74 mg, 59%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.74 (d, J=9.6 Hz, 1H), 7.62 (s, 1H), 6.85 (d, J=9.6 Hz, 1H), 6.71-6.62 (m, 2H), 3.83 (t, J=6.3 Hz, 2H), 3.51 (t, J=6.4 Hz, 2H), 3.34 (q, J=7.0 Hz, 4H), 2.32-2.39 (m, 2H), 1.54-1.48 (m, 2H), 1.46-1.40 (m, 2H), 1.38-1.34 (t, J=7.3 Hz, 6H), 0.96 (t , J=7.3 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 155.7, 136.6, 135.3, 129.5, 125.7, 125.1, 115.8, 115.4, 51.0, 37.6, 34.4, 32.7, 23.4, 14.3, 9.2 (one signal overlapping with solvent); HPLC tR=9.3 min (Luna), 96.7%; ES-MS: (M+H)=316 m/z.

Sources & evidence

ORD record
ord-09633e4ec8bd48ef9a0ec41a38562291
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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