Pyridine → 2-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetonitrile

HRID 462460Notes

Reaction equation

HRID 462460 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=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]([NH2:37])=O)=[C:22]1[C:38]([O:40][CH2:41][CH3:42])=[O:39].N1C=CC=CC=1>O1CCOCC1.O>[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=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]#[N:37])=[C:22]1[C:38]([O:40][CH2:41][CH3:42])=[O:39]

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 134572222-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetamide

Product 1

HCID 134572262-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetonitrileYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of trifluoroacetic anhydride (0.56 g) in dioxane (5 ml) was added dropwise over 5 minutes to a stirred, ice-cooled solution of 2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetamide (0.84 g) and pyridine (0.32 g) in dioxane (25 ml). The mixture was stirred at room temperature for 4 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over sodium sulphate and evaporated. The residue was purified by chromatography on silica (10 g) eluting with dichloromethane plus 0-2% v/v methanol. Appropriate fractions were combined and evaporated to give the title compound (0.60 g), m.p. 128°-130° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica (10 g)
  7. washeluting with dichloromethane plus 0-2% v/v methanol
  8. customevaporated

Sources & evidence

ORD record
ord-6bcb9239bd27494e90f744096a078ce4
Source dataset
uspto-grants-1985_05
Patent number
US04515799

Reaction notes

Loading…