Potassium Carbonate → HCID 14708781, compound

HRID 1589644Notes

Reaction equation

HRID 1589644 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[NH2:7][CH2:8][CH2:9][O:10][CH2:11][C:12]1[NH:13][C:14]([CH3:35])=[C:15]([C:31]([O:33][CH3:34])=[O:32])[CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=2[Cl:30])[C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:30][C:24]1[C:25]([Cl:29])=[CH:26][CH:27]=[CH:28][C:23]=1[CH:16]1[C:15]([C:31]([O:33][CH3:34])=[O:32])=[C:14]([CH3:35])[NH:13][C:12]([CH2:11][O:10][CH2:9][CH2:8][NH:7][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[C:17]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 13663190HCID 13663190, compound

Product 1

HCID 14708781HCID 14708781, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of methyl bromoacetate (1.53 g) in acetonitrile (20 ml) was added dropwise over 30 minutes to a stirred, refluxing mixture of 2-[(2-aminoethoxy)methyl]-4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (5.01 g) and potassium carbonate (2.76 g) in acetonitrile (60 ml). The mixture was then heated under reflux for 3 hours, filtered, and evaporated. The residue was partitioned between ethyl acetate and water and the organic layer washed with water, dried (Na2SO4), and evaporated. The residue was chromatographed on silica (t.l.c. grade Merck Kieselgel 60H, [Trade Mark] 40 g) eluting with dichloromethane plus 0-3% methanol. Appropriate fractions were combined and evaporated to give the title compound (2.10 g), m.p. 96°-98°.

Workup

  1. temperaturerefluxing
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux for 3 hours
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was partitioned between ethyl acetate and water
  7. washthe organic layer washed with water
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customThe residue was chromatographed on silica (t.l.c. grade Merck Kieselgel 60H, [Trade Mark] 40 g)
  11. washeluting with dichloromethane plus 0-3% methanol
  12. customevaporated

Sources & evidence

ORD record
ord-3c38d60894704482864f129f63f075bc
Source dataset
uspto-grants-1986_02
Patent number
US04572909

Reaction notes

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