Chlorosuccinimide → HCID 11210651, compound

HRID 2356246Notes

Reaction equation

HRID 2356246 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][N:15]3[CH:24]=2)=[CH:8][CH:7]=1.[Cl:25]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][N:15]3[C:24]=2[Cl:25])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11381836HCID 11381836, compound

Product 1

HCID 11210651HCID 11210651, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred mixture of 2-[4-(2-methoxyethoxy)phenyl]-6-propoxyimidazo[1,2-b] pyridazine (164 mg, 0.50 mmol), N-chlorosuccinimide (67 mg, 29.4 mmol) and chloroform (3 mL) was heated under reflux for 1.5 hours. The mixture was cooled and washed with saturated aqueous sodium bicarbonate solution, dried (MgSO4) and evaporated. The residue was purified by radial chromatography on silica gel. Elution with 0-2% methanol in dichloromethane afforded Compound 91 (158 mg, 87%) as an off-white solid. 1H n.m.r. (CDCl3) δ 1.07, t, J=7.5 Hz, 3H; 1.75-2.0, m, 2H; 3.47, s, 3H; 3.78, t, J=4 Hz, 2H; 4.19, t, J=4 Hz, 2 H; 4.38, t, J=6.5 Hz, 2H; 6.74, d, J=9.5 Hz, 1H; 7.04, d, J=8.5 Hz, 2H; 7.81, d, J=9.5 Hz, 1H; 8.06, d, J=8.5 Hz, 2H. Mass spectrum (APCI+) m/z 362/364 (M+H, 100%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureThe mixture was cooled
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by radial chromatography on silica gel
  8. washElution with 0-2% methanol in dichloromethane afforded Compound 91 (158 mg, 87%) as an off-white solid

Sources & evidence

ORD record
ord-6c49236f10634f6abf4e5986bcb289c2
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

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