N-bromobutanimide → N-{5-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-4-methyl-oxazol-2-yl}-dimethylamine

HRID 1432596Notes

Reaction equation

HRID 1432596 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[O:21][CH:20]=[N:19][C:18]=3[CH3:22])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C1[C:28](=O)[N:27](Br)[C:25](=O)C1>C(Cl)Cl>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[O:21][C:20]([N:27]([CH3:28])[CH3:25])=[N:19][C:18]=3[CH3:22])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 579329208-(1-Ethyl-propyl)-2,6-dimethyl-3-(4-methyl-oxazol-5-yl)-imidazo[1,2-b]pyridazine

Product 1

HCID 57932997N-{5-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-4-methyl-oxazol-2-yl}-dimethylamineYield 13.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

230 mg of 8-(1-Ethyl-propyl)-2,6-dimethyl-3-(4-methyl-oxazol-5-yl)-imidazo[1,2-b]pyridazine (0.77 mmol) is dissolved in 20 ml of CH2Cl2 and 178 mg of NBS (1.0 mmol) is added. The reaction mixture is stirred at room temperature overnight. The reaction mixture is washed with sat. Na2S2O3, sat. NaCl, dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane:AcOEt=3:1) to give 36 mg of the title compound. Yield 12%. mass spectrum (m/e): 378 (M+1). 1H-NMR (CDCl3): 6.82 (s, 1H), 3.39 (m, 1H), 2.58 (s, 3H), 2.53 (s, 3H), 2.26 (s, 3H), 1.85 (m, 1H), 0.89 (t, J=7.4 Hz, 6H).

Workup

  1. washThe reaction mixture is washed with sat. Na2S2O3, sat. NaCl
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-70bb00d547da40ecaf62391e8f974291
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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