Amlodipine → HCID 70381129, compound

HRID 280577Notes

Reaction equation

HRID 280577 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].[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([NH:36][S:37](Cl)(=[O:39])=[O:38])=[O:35]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[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][S:37]([NH:36][C:34]([C:30]2[O:29][CH:33]=[CH:32][CH:31]=2)=[O:35])(=[O:38])=[O:39])=[C:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 2

HCID 2162AmlodipineHCID 23320835HCID 23320835, compound

Product 1

HCID 70381129HCID 70381129, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (0.5 g) in chloroform (dried over alumina) and triethylamine (2 ml) was added 2-furoylsulphamoyl chloride in one portion and the mixture stirred at room temperature for 17 hours. After evaporation to dryness, the resultant oil was partitioned between 5% aqueous sodium bicarbonate and methylene chloride. The combined organic liquors were dried (MgSO4), filtered and evaporated to give 0.35 g of solid which was crystallised from diisopropyl ether to give pure title compound (0.2 g), m.p. 138° C. Found: C, 51.30; H, 5.23; N, 7.41. C25H28ClN3O9S requires C, 51.59; H, 4.85; N, 7.22%.

Workup

  1. customAfter evaporation to dryness
  2. customthe resultant oil was partitioned between 5% aqueous sodium bicarbonate and methylene chloride
  3. dry with materialThe combined organic liquors were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3b8d885e03f74295af7c4736c1dca6b6
Source dataset
uspto-grants-1986_05
Patent number
US04590195

Reaction notes

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