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

HRID 464637Notes

Reaction equation

HRID 464637 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([CH3:30])[NH:23][C:22]([CH2:31][O:32][CH2:33][C:34](O)=[O:35])=[C:21]1[C:37]([O:39][CH2:40][CH3:41])=[O:38].N>O1CCCC1>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]([CH3:30])[NH:23][C:22]([CH2:31][O:32][CH2:33][C:34]([NH2:3])=[O:35])=[C:21]1[C:37]([O:39][CH2:40][CH3:41])=[O:38]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 13457220{[4-(2-Chlorophenyl)-3-(ethoxycarbonyl)-5-(methoxycarbonyl)-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetic acid

Product 1

HCID 134572222-{[4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetamideYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (9.80 g) was added to a suspension of 2-{[4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxy}acetic acid (25.4 g) in tetrahydrofuran (400 ml) and the mixture stirred at room temperature for 2 hours. A stream of gaseous ammonia was passed through the resulting solution with stirring until the reaction was complete (as determined by t.l.c.). The reaction mixture was evaporated and the residue partitioned between ethyl acetate and water. The organic layer was washed with water, dried over sodium sulphate and evaporated. The residue was triturated with diethyl ether and the resulting solid collected, recrystallised from diethyl ether/n-hexane and dried to give the title compound (17.0 g), m.p. 127°-128° C. Found: C,56.70; H,5.42; N,6.60. C20H23ClN2O6 requires: C,56.60; H,5.48; N,6.63%.

Workup

  1. stirringwith stirring until the reaction
  2. customThe reaction mixture was evaporated
  3. customthe residue partitioned between ethyl acetate and water
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe residue was triturated with diethyl ether
  8. customthe resulting solid collected
  9. customrecrystallised from diethyl ether/n-hexane
  10. customdried

Sources & evidence

ORD record
ord-485f58a7e8b444ae97d8c645e977e9ea
Source dataset
uspto-grants-1985_10
Patent number
US04548935

Reaction notes

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