N-bromobutanimide → HCID 57932944, compound

HRID 1432631Notes

Reaction equation

HRID 1432631 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[CH:21]=[CH:20][S: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].C1C(=O)N([Br:30])C(=O)C1>C(Cl)Cl>[Br:30][C:20]1[S:19][C:18]([CH3:22])=[C:17]([C:13]2[N:8]3[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]3=[N:15][C:14]=2[CH3:16])[CH:21]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57933037HCID 57933037, compound

Product 1

HCID 57932944HCID 57932944, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(1-ethyl-propyl)-2,6-dimethyl-3-(2-methyl-thiophen-3-yl)-imidazo[1,2-b]pyridazine. (0.76 g, 2.42 mmol) and CH2Cl2 (10 mL) is added NBS (0.60 g, 3.37 mmol). The solution is stirred at ambient temperature for 2 hours and concentrated. The solution is dissolved in Et2O (30 mL) washed with water (3×30 mL), brine (30 mL) dried over MgSO4, filtered and concentrated to furnish the title compound (0.95 g, 2.42 mmol, >99%). 1H NMR (CDCl3), δ 0.88 (t, J=7.5 Hz, 6H), 1.74-1.93 (m, 4H), 2.31 (s, 3H), 2.42 (s, 3H), 2.51 (s, 3H), 3.29-3.38 (m, 1H), 6.66 (s, 1H), 7.04 (s, 1H). LC/MS (m/z): calcd. for C18H22BrN3S (M+H)+: 392.2; found: 392.1.

Workup

  1. concentrationconcentrated
  2. dissolutionThe solution is dissolved in Et2O (30 mL)
  3. washwashed with water (3×30 mL), brine (30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d2baee51a5e24efd8c53456e292c56c2
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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