Pyridine → HCID 20070377, compound

HRID 1721884Notes

Reaction equation

HRID 1721884 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12](C)[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][N:23]2[C:27]([CH3:28])=[C:26]([CH3:29])[N:25]=[C:24]2[CH3:30])=[C:9]1[C:31]([O:33][CH2:34][CH3:35])=[O:32].N1C=CC=CC=1.C1C=C[NH+]=CC=1.Br[Br-]Br>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:9]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:10]([CH2:19][O:20][CH2:21][CH2:22][N:23]2[C:27]([CH3:28])=[C:26]([CH3:29])[N:25]=[C:24]2[CH3:30])[NH:11][C:12]2[CH2:17][O:16][C:14](=[O:15])[C:13]1=2

Participants

4

Reactant 2

HCID 1049PyridineHCID 13457165HCID 13457165, compound

Product 1

HCID 20070377HCID 20070377, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-(2,4,5-trimethylimidazol-1-yl)ethoxymethyl]-1,4-dihydropyridine (3.0 g) in chloroform (50 cm3) stirred at 0° C. under N2 was treated with pyridine (790 mg) followed by pyridinium bromide perbromide (2.1 g) in portions over five minutes and the mixture stirred at 0° C. for one hour and then heated at reflux temperature for three hours. The solution was cooled, washed with 2N hydrochloric acid (2×50 cm3) and brine (50 cm3), dried over MgSO4, filtered and evaporated to dryness. The residue was purified by silica-gel column chromatography eluting with diethylamine/ethyl acetate (1:9). The appropriate fractions were evaporated to dryness and taken up in ethyl acetate (25 cm3) from which the title compound crystallised as a colourless solid (440 mg). M.p. 215°-217° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for three hours
  3. temperatureThe solution was cooled
  4. washwashed with 2N hydrochloric acid (2×50 cm3) and brine (50 cm3)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by silica-gel column chromatography
  9. washeluting with diethylamine/ethyl acetate (1:9)
  10. customThe appropriate fractions were evaporated to dryness
  11. customcrystallised as a colourless solid (440 mg)

Sources & evidence

ORD record
ord-d804d751e07c4458b912956550e75ac6
Source dataset
uspto-grants-1989_08
Patent number
US04853392

Reaction notes

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