Pyridine → HCID 19871309, compound

HRID 329693Notes

Reaction equation

HRID 329693 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=O.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH:21]1[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([CH3:31])[NH:24][C:23]([CH2:32][O:33][CH2:34][C:35](O)=[O:36])=[C:22]1[C:38]([O:40][CH2:41][CH3:42])=[O:39].N1C=CC=CC=1.CC1(C)OC(=O)CC(=O)O1>ClCCl>[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH:21]1[C:26]([C:27]([O:29][CH3:30])=[O:28])=[C:25]([CH3:31])[NH:24][C:23]([CH2:32][O:33][CH2:34][C:35]([CH3:1])=[O:36])=[C:22]1[C:38]([O:40][CH2:41][CH3:42])=[O:39]

Participants

6

Reactant 4

HCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 13457221HCID 13457221, compound

Product 1

HCID 19871309HCID 19871309, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of carbonyl diimidazole (8.00 g) and 2-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}acetic acid (20.00 g) (see European patent application publication No. 0100189) in dichloromethane (400 ml) was stirred at room temperature under nitrogen for 2 hours and then added to a solution of pyridine (3.60 g) and 2,2-dimethyl-1,3-dioxan-4,6-dione (6.50 g) in dichloromethane over 5 minutes. The mixture was stirred at room temperature for 2 days, washed successively with ice-cooled 2.5M hydrochloric acid and saturated brine, dried over magnesium sulphate and evaporated. The residue was dissolved in water (300 ml) and acetic acid (150 ml) and refluxed for 5 hours. The mixture was evaporated and partitioned between diethyl ether (800 ml) and 10% aqueous sodium carbonate. The ether solution was dried over magnesium sulphate and evaporated. The residue was chromatographed on silica (50 g) using 30% hexane in dichloromethane as the eluant. Fractions which contained the pure product were evaporated to give the title compound (6.5 g), m.p. 117°-119°.

Workup

  1. washwashed successively with ice-
  2. temperaturecooled 2.5M hydrochloric acid and saturated brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. dissolutionThe residue was dissolved in water (300 ml)
  6. temperatureacetic acid (150 ml) and refluxed for 5 hours
  7. customThe mixture was evaporated
  8. custompartitioned between diethyl ether (800 ml) and 10% aqueous sodium carbonate
  9. dry with materialThe ether solution was dried over magnesium sulphate
  10. customevaporated
  11. customThe residue was chromatographed on silica (50 g)
  12. customwere evaporated

Sources & evidence

ORD record
ord-8e748a9409b344fabcdfcc8e8fb6a018
Source dataset
uspto-grants-1990_01
Patent number
US04892881

Reaction notes

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