B-(1E)-1-Hexenylboronic acid → (E)-tert-Butyl 3-(3-(hex-1-enyl)imidazo[1,2-b]pyridazin-6-ylamino)propylcarbamate

HRID 1162144Notes

Reaction equation

HRID 1162144 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:23](/B(O)O)=[CH:24]\[CH2:25][CH2:26][CH2:27][CH3:28].C(Cl)Cl.CO.[NH4+].[OH-]>>[CH:23](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:24]\[CH2:25][CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 3

HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 21896990Dichloromethane methanol ammonium hydroxideHCID 57470631tert-Butyl 3-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)propylcarbamate

Product 1

HCID 86621015(E)-tert-Butyl 3-(3-(hex-1-enyl)imidazo[1,2-b]pyridazin-6-ylamino)propylcarbamate

Procedure

Prepared from the product from step A and (E)-1-hexeneboronic acid according to general procedure 2 providing the crude Boc-protected olefin (122 mg, 96%) as a brown oil: Rf=0.71 (CH2Cl2/MeOH/NH4OH, 160:18:2); 1H NMR (500 MHz, CD3OD) δ 7.78 (d, J=9.7 Hz, 1H), 7.54 (s, 1H), 6.64-6.40 (m, 3H), 3.47 (q, J=6.3 Hz, 2H), 3.29-3.23 (m, 2H), 2.36-2.30 (m, 2H), 1.84-1.81 (m, 2H), 1.50-1.42 (m, 11H), 1.40-1.48 (m, 2H), 0.93 (t, J=7.3 Hz, 3H).

Sources & evidence

ORD record
ord-93dc3da2d77c43cfa215d510e480f9f1
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

Loading…