Pyridine → HCID 58095189, compound

HRID 2282155Notes

Reaction equation

HRID 2282155 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[NH:8][CH:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][N:11]=2)=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[C:3]=1[C:24]#[N:25].C(Cl)(Cl)(Cl)Cl.C(#N)C.N1C=CC=CC=1.N12CCCN=C1CCCCC2>>[Br:1][C:2]1[S:6][C:5]([C:7]2[NH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:11]=2)=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[C:3]=1[C:24]#[N:25]

Participants

6

Reactant 5

HCID 1049PyridineHCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58094889HCID 58094889, compound

Product 1

HCID 58095189HCID 58095189, compoundYield 67%

Procedure

To a mixture of methyl 2-[5-bromo-4-cyano-3-(2,4-dichlorophenyl)-2-thienyl]-4,5-dihydro-1H-imidazole-5-carboxylate (0.341 g, 0.743 mmol), carbon tetrachloride (12.1 mL, 126 mmol), acetonitrile (18.3 mL, 351 mmol) and pyridine (12 mL, 150 mmol) was added 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.442 mL, 2.96 mmol) slowly. The solution was stirred at room temperature for 16 hours. The mixture was evaporated, then the residue was diluted with dichloromethane and 0.5N aqueous HCl solution. The layers were separated, then the organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (0.226 g, 67%). LCMS: (FA) ES+, 458. 1H NMR (400 MHz, d4-Methanol) δ: 7.70-7.67 (m, 2H), 7.53-7.43 (m, 2H), 3.85 (s, 3H).

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was diluted with dichloromethane and 0.5N aqueous HCl solution
  3. customThe layers were separated
  4. washthe organic extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-958bf3c24cc040febf4228359f1089a0
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

Loading…