Sodium Bicarbonate → HCID 178424922, compound

HRID 1896046Notes

Reaction equation

HRID 1896046 reaction equation
[N+]([N:4]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[N:6]=[CH:5]1)([O-])=O.C(=O)([O-])O.[Na+].[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[C:25][CH:26]=[C:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[N:19]=1>O.CC(C)=O>[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[C:25][CH:26]=[C:27]2[CH2:28][CH2:29][N:30]([C:8]3[NH:4][CH:5]=[N:6][C:7]=3[N+:9]([O-:11])=[O:10])[CH2:31][CH2:32]2)[N:19]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 51694961,4-Dinitro-1H-imidazoleHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 178424922HCID 178424922, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of 1,4-dinitroimidazole (207 mg, 1.31 mmol) and sodium hydrogencarbonate (242 mg, 2.88 mmol) in 4 mL of water and 0.16 mL of acetone was added drop wise a solution of the compound of Example 3 (278 mg, 1.31 mmol) in acetone. The reaction mixture was refluxed for 2 h, poured into water and extracted with EtOAc. The crude residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with EtOAc-MeOH gradient from 1:0 to 92:8; affording the title compound not enough pure. So, it was purified again by preparative RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient affording 4 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. extractionextracted with EtOAc
  3. customThe crude residue was purified by automated flash liquid chromatography (Horizon™-Biotage)
  4. washeluting with EtOAc-MeOH gradient from 1:0 to 92:8

Sources & evidence

ORD record
ord-fd206c0e03764d52b5e84db950412ddc
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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