B-(1E)-1-Hexenylboronic acid → (E)-N1-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-yl)-N4,N4-dimethylbutane-1,4-diamine

HRID 1162140Notes

Reaction equation

HRID 1162140 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[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]>>[CH:19](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:20]\[CH2:21][CH2:22][CH2:23][CH3:24]

Participants

3

Reactant 2

HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 68648035N1-(3-Bromoimidazo[1,2-b]pyridazin-6-yl)-N4,N4-dimethylbutane-1,4-diamine

Product 1

HCID 59519586(E)-N1-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-yl)-N4,N4-dimethylbutane-1,4-diamineYield 42%

Procedure

Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2 providing the title compound (51 mg, 42%) as a brown solid; 1H NMR (300 MHz, CDCl3) δ 7.54 (d, J=9.5 Hz, 1H), 7.49 (s, 1H), 6.72-6.58 (m, 2H), 6.32 (d, J=9.5 Hz, 1H), 5.60 (br, 1H), 3.39 (q, J=6.2 Hz, 2H), 2.38 (t, J=6.7 Hz, 1H), 2.31-2.22 (m, 8H), 1.78-1.72 (m, 2H), 1.69-1.63 (m, 2H), 1.52-1.36 (m, 4H), 0.94 (t, J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 153.3, 136.9, 131.4, 129.4, 127.2, 125.7, 115.9, 110.5, 59.2, 45.1, 41.8, 33.4, 31.7, 26.9, 25.4, 22.3, 13.9; HPLC tR=11.4 min (Luna), 96.8%; ES-MS: (M+H)=316 m/z.

Sources & evidence

ORD record
ord-fc337c8f5b4542cf9235d972ead0a05d
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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