Hydrochloric Acid → (E)-N1-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-yl)-N3,N3-dimethylpropane-1,3-diamine hydrochloride

HRID 1162126Notes

Reaction equation

HRID 1162126 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:18](/B(O)O)=[CH:19]\[CH2:20][CH2:21][CH2:22][CH3:23].[ClH:27]>CCOCC>[ClH:27].[CH:18](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:19]\[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 68648083N1-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)-N3,N3-dimethylpropane-1,3-diamine

Product 1

HCID 68647709(E)-N1-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-yl)-N3,N3-dimethylpropane-1,3-diamine hydrochlorideYield 40%

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 (31 mg, 40%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.63 (d, J=9.7 Hz, 1H), 7.55 (s, 1H), 6.74 (d, J=9.7 Hz, 1H), 6.69-6.66 (m, 2H), 3.52 (t, J=6.5 Hz, 2H), 3.29-3.26 (m, 2H), 2.90 (s, 6H), 2.32-2.38 (m, 2H), 2.18-2.16 (m, 2H), 1.54-1.48 (m, 2H), 1.46-1.39 (m, 2H), 0.96 (t, J=7.3 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 155.6, 137.0, 134.2, 129.1, 126.8, 125.0, 116.3, 114.7, 57.3, 43.6, 38.5, 34.4, 23.8, 25.1, 23.1, 14.3; HPLC tR=9.2 min (Luna), 97.9%; ES-MS: (M+H)=302 m/z.

Sources & evidence

ORD record
ord-0fc8902216314031abb017d8cfe8a99d
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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