Dichloromethane → HCID 57932902, compound

HRID 1432644Notes

Reaction equation

HRID 1432644 reaction equation
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:17]3[S:18][CH:19]=[CH:20][C:21]=3[C:22]#[N:23])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C(Cl)Cl.C1C(=O)N([Br:34])C(=O)C1>CCOCC>[Br:34][C:19]1[S:18][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])=[C:21]([C:22]#[N:23])[CH:20]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 579330472-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-thiophene-3-carbonitrile

Product 1

HCID 57932902HCID 57932902, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-thiophene-3-carbonitrile (0.83 g, 2.56 mmol) and CH2Cl2 (10 mL) is added NBS (0.48 g, 2.69 mmol). The solution is stirred for 1 hour, diluted with Et2O (100 mL), washed with water (3×100 mL), brine (100 mL), dried (MgSO4) filtered and concentrated to furnish the title compound (1.03 g, 2.55 mmol, >99%). 1H NMR (CDCl3) δ 0.86 (t, J=7.5 Hz, 6H), 1.74-1.91 (m, 4H), 2.56 (s, 3H), 2.60 (s, 3H), 3.24-3.32 (m, 1H), 6.76 (s, 1H), 7.30 (s, 1H). LC/MS (m/z): calcd. for C18H19BrN4S (M+H)+: 404.4; found: 404.1.

Workup

  1. washwashed with water (3×100 mL), brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e204e02f538a4efc85b20e84ddde6fb0
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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