Ammonia → HCID 9912345, compound

HRID 1589645Notes

Reaction equation

HRID 1589645 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][NH:23][CH2:24][C:25](OCC)=[O:26])=[C:9]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].[NH3:35]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:18])[NH:11][C:10]([CH2:19][O:20][CH2:21][CH2:22][NH:23][CH2:24][C:25]([NH2:35])=[O:26])=[C:9]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14708782HCID 14708782, compound

Product 1

HCID 9912345HCID 9912345, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-(2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}ethyl)aminoacetate (2.50 g) in a mixture of ethanol (40 ml) and 0.880 aqueous ammonia (30 ml) was stirred at room temperature for four days and then evaporated. The residue was partitioned between ethyl acetate and water and the organic layer washed with water, dried (MgSO4), and evaporated. The residue was chromatographed on silica (t.l.c. grade Merck Kieselgel 60H, [Trade Mark] 30 g) eluting with dichloromethane plus 0-5% methanol. Appropriate fractions were combined and evaporated. The residue was triturated with ethyl acetate and the resulting solid collected, washed with ethyl acetate, and dried to give the title compound (1.23 g), m.p. 126°-129°.

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica (t.l.c. grade Merck Kieselgel 60H, [Trade Mark] 30 g)
  7. washeluting with dichloromethane plus 0-5% methanol
  8. customevaporated
  9. customThe residue was triturated with ethyl acetate
  10. customthe resulting solid collected
  11. washwashed with ethyl acetate
  12. customdried

Sources & evidence

ORD record
ord-373971c93d4a46ebb37c59fada89f0b8
Source dataset
uspto-grants-1986_02
Patent number
US04572909

Reaction notes

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