3-Bromo-6-(butylamino)imidazo[1,2-b]pyridazine → HCID 136378623, compound

HRID 870689Notes

Reaction equation

HRID 870689 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[NH:34][C:33](=[O:35])[O:32][N:31]=3)=[CH:26][CH:25]=2)O1>>[CH2:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[NH:34][C:33](=[O:35])[O:32][N:31]=4)=[CH:26][CH:25]=3)=[CH:3][N:4]=2)[N:7]=1)[CH2:13][CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 866963223-Bromo-6-(butylamino)imidazo[1,2-b]pyridazineHCID 136378622HCID 136378622, compound

Product 1

HCID 136378623HCID 136378623, compoundYield 25.3%

Procedure

Following the Suzuki coupling conditions described in example 5.6.45 from (3-bromo-imidazo[1,2-b]pyridazin-6-yl)-butyl-amine (213.1 mg, 0.8 mmol), and 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one (308.2 mg, 1.1 mmol) to provide 70.9 mg of 3-[4-(6-butylamino-imidazo[1,2-b]pyridazin-3-yl)-phenyl]-4H-[1,2,4]oxadiazol-5-one as white crystalline powder, mp. 253-254° C. (dec.). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96 (t, J=7.33 Hz, 3H) 1.44 (sxt, J=7.38 Hz, 2H) 1.65 (quin, J=7.26 Hz, 2H) 3.26-3.35 (m, 2H) 6.75 (d, J=9.85 Hz, 1H) 7.15 (t, J=5.31 Hz, 1H) 7.77 (d, J=9.60 Hz, 1H) 7.88 (m, J=8.84 Hz, 2H) 8.05 (s, 1H) 8.44 (m, J=8.59 Hz, 2H). 13C NMR (100 MHz, DMSO-d6) δ ppm 13.73, 19.89, 30.15, 40.81, 112.82, 120.91, 125.38, 125.50, 126.11, 131.05, 133.01, 137.80, 153.62, 157.06, 159.94. LRMS (ESI) m/z 351.2 [(M+H)]+, calc'd for C18H18N6O2: 350.38.

Sources & evidence

ORD record
ord-c88634829edf4c36bc0fbfbb4521e24e
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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