Pyridine → HCID 14547435, compound

HRID 1589150Notes

Reaction equation

HRID 1589150 reaction equation
C(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(O)=O)=[C:22]1[C:38]([O:40][CH2:41][CH3:42])=[O:39].N1C=CC=CC=1.C[C:50]1([CH3:58])[O:55][C:54](=[O:56])[CH2:53][C:52](=[O:57])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:52](=[O:57])[CH2:53][C:54]([O:55][CH2:50][CH3:58])=[O:56])=[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 14547435HCID 14547435, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of carbonyl diimidazole (5.20 g) and 2-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetic acid (14.00 g) in dichloromethane (200 ml) was stirred at room temperature under nitrogen for 2 hours and then added to a solution of pyridine (2.40 g) and 2,2-dimethyl-1,3-dioxane-4,6-dione (4.56 g) in dichloromethane (200 ml) over 8 minutes. The mixture was stirred at room temperature for 2.5 hours, washed successively with water, ice-cold 2.5M hydrochloric acid and saturated brine, dried over anhydrous magnesium sulphate and evaporated. The residue was dissolved in ethanol (200 ml) and the solution heated under reflux for 2.75 hours and evaporated. The residue was triturated with diethyl ether and the resulting solid collected washed with diethyl ether and dried to give the title compound (9.0 g), m.p. 99°-102° C.

Workup

  1. washwashed successively with water, ice-cold 2.5M hydrochloric acid and saturated brine
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethanol (200 ml)
  5. temperaturethe solution heated
  6. temperatureunder reflux for 2.75 hours
  7. customevaporated
  8. customThe residue was triturated with diethyl ether
  9. customthe resulting solid collected
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-9a373a951b66416a93794ec41003609f
Source dataset
uspto-grants-1986_02
Patent number
US04568677

Reaction notes

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