Pyridine → HCID 19871309, compound

HRID 1906769Notes

Reaction equation

HRID 1906769 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) 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-cold 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 "Kieselgel 60-H" (Trade Mark) silica (50 g) using 30% hexane in dichloromethane. 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-cold 2.5M hydrochloric acid and saturated brine
  2. dry with materialdried over magnesium sulphate
  3. customevaporated
  4. dissolutionThe residue was dissolved in water (300 ml)
  5. temperatureacetic acid (150 ml) and refluxed for 5 hours
  6. customThe mixture was evaporated
  7. custompartitioned between diethyl ether (800 ml) and 10% aqueous sodium carbonate
  8. dry with materialThe ether solution was dried over magnesium sulphate
  9. customevaporated
  10. customThe residue was chromatographed on "Kieselgel 60-H" (Trade Mark) silica (50 g)
  11. customwere evaporated

Sources & evidence

ORD record
ord-7bc3b2a6fbd84b83a4802840238df0b6
Source dataset
uspto-grants-1987_03
Patent number
US04654353

Reaction notes

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