B-(1E)-1-Hexenylboronic acid → (E)-3-(Hex-1-enyl)-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine

HRID 1162105Notes

Reaction equation

HRID 1162105 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:21](/B(O)O)=[CH:22]\[CH2:23][CH2:24][CH2:25][CH3:26]>>[CH:21](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:22]\[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

3

Reactant 2

HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 686478363-Bromo-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine

Product 1

HCID 68648539(E)-3-(Hex-1-enyl)-N-(3-morpholinopropyl)imidazo[1,2-b]pyridazin-6-amine

Procedure

Prepared from the product of step A (example 16) and (E)-1-hexeneboronic acid according to general procedure 2 providing the alkene (100 mg, 90%) as a brown oil; 1H NMR (500 MHz, CD3OD) δ 7.51 (d, J=9.6 Hz, 1H), 7.41 (s, 1H), 6.75 (dt, J=7.0, 16.1 Hz, 1H), 6.62-6.58 (m, 2H), 3.70 (t, J=4.8 Hz, 4H), 3.41 (t, J=6.9 Hz, 2H), 2.52 (m, 6H), 2.30-2.26 (m, 2H), 1.94-1.88 (m, 2H), 1.52-1.41 (m, 4H), 0.96 (t, J=7.3 Hz, 3H).

Sources & evidence

ORD record
ord-93cb4a9638ea4682b7cbde90bae0a785
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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