Amlodipine → 4-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-{2-[(2-chloro-5-pyridyl)sulphonamido]ethoxymethyl}-1,4-dihydropyridine

HRID 280574

Reaktionsgleichung

Reaktionsgleichung von HRID 280574
[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(N(CC)CC)C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][N:38]=1>ClCCl>[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:43]([C:40]2[CH:41]=[CH:42][C:37]([Cl:36])=[N:38][CH:39]=2)(=[O:45])=[O:44])=[C:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

5

Edukt 3

HCID 2162AmlodipineHCID 8471TriethylamineHCID 27927922-Chloro-5-pyridinesulfonyl chloride

Produkt 1

HCID 233208404-(2-Chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-{2-[(2-chloro-5-pyridyl)sulphonamido]ethoxymethyl}-1,4-dihydropyridineAusbeute 54,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (409 mg) and triethylamine (202 mg) in dry dichloromethane (20 ml) was stirred under nitrogen and cooled in an ice-bath while a solution of 2-chloro-5-pyridinesulphonyl chloride (212 mg) in dry dichloromethane (10 ml) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirring continued for a further 3 hours. The solvent was evaporated and the residue chromatographed on silica, eluting with dichloromethane. Appropriate fractions were combined and evaporated and the residue recrystallised from ethyl acetate to give the title compound (320 mg), m.p. 140°-140.5° C. Found: C, 51,27; H, 4.63; N, 7.25. C25H27Cl2N3O7 requires C, 51.37; H, 4.66; N, 7.19%.

Aufarbeitung

  1. additionwas added dropwise
  2. customThe solvent was evaporated
  3. customthe residue chromatographed on silica
  4. washeluting with dichloromethane
  5. customevaporated
  6. customthe residue recrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5c341f7cd88d44d39d32fefb43089a7a
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04590195

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