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

HRID 462459Notes

Reaction equation

HRID 462459 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.

Workup

  1. stirringwith stirring until the reaction
  2. customwas 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-25354d5dae334d98b0c528a1382bde84
Source dataset
uspto-grants-1985_05
Patent number
US04515799

Reaction notes

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