B-(1E)-1-Hexenylboronic acid → (E)-2-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-ylamino)butan-1-ol

HRID 1162101Notes

Reaction equation

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

Participants

Reactant 2

HCID 5326225B-(1E)-1-Hexenylboronic acid

HCID 574706232-(3-Bromoimidazo[1,2-b]pyridazin-6-ylamino)butan-1-ol

Product 1

HCID 59519594(E)-2-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-ylamino)butan-1-olYield 38%

Procedure

Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2 providing the title compound (27 mg, 38%) as an off-white solid; 1H NMR (500 MHz, CD3OD) δ 7.51 (d, J=9.7 Hz, 1H), 7.40 (s, 1H), 6.76-6.70 (m, 1H), 6.66 (d, J=9.7 Hz, 1H), 6.61 (d, J=16.1 Hz, 1H), 3.93-3.89 (m, 1H), 3.70-3.67 (m, 2H), 2.35-2.30 (m, 2H), 1.81-1.76 (m, 1H), 1.69-1.65 (m, 1H), 1.53-1.48 (m, 2H), 1.45-1.40 (m, 2H), 1.04-1.01 (t, J=7.3 Hz, 3H), 0.55 (t, J=7.3 Hz, 3H); 13C NMR (75 MHz, CD3OD) δ 155.6, 138.2, 133.3, 129.1, 128.9, 125.8, 117.2, 114.1, 64.2, 56.1, 34.8, 33.2, 35.4, 23.7, 14.7, 11.4; HPLC tR=12.9 min (Luna), 95.1%; ES-MS: (M+H)=289 m/z.

Sources & evidence

ORD record: ord-06d4c99034b6463fa93b7f6ac96d601b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820670B2

Reaction notes

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