Amlodipine → HCID 14528697, compound

HRID 1589151Notes

Reaction equation

HRID 1589151 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][C:6]1[NH:7][C:8]([CH3:28])=[C:9]([C:24]([O:26][CH3:27])=[O:25])[CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[C:29](N1C=CN=C1)([N:31]1[CH:35]=[CH:34][N:33]=[CH:32]1)=[O:30].CN1CCOCC1>O1CCCC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH:10]1[C:9]([C:24]([O:26][CH3:27])=[O:25])=[C:8]([CH3:28])[NH:7][C:6]([CH2:5][O:4][CH2:3][CH2:2][NH:1][C:29]([N:31]2[CH:35]=[CH:34][N:33]=[CH:32]2)=[O:30])=[C:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 2162AmlodipineHCID 79724-MethylmorpholineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 14528697HCID 14528697, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2-aminoethoxy)methyl-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (20.4 g), carbonyldiimidazole (8.9 g) and N-methylmorpholine (20 ml) in tetrahydrofuran (500 ml) was stirred at room temperature for 2 hours and then evaporated. The residue was partitioned between ethyl acetate and water and the organic layer washed with water, dried (Na2SO4), and evaporated. The residual solid was washed with diethyl ether and dried to give the title compound (16.6 g), m.p. 149°-151° C. Found: C,57.35; H,5.54; N,11.22. C24H27ClN4O6 requires: C,57.54; H,5.43; N,11.18%.

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. washThe residual solid was washed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-8c486df0253f495180fb944e056fc961
Source dataset
uspto-grants-1986_02
Patent number
US04568677

Reaction notes

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