Sodium Iodide → 5-(2-cyanomethylaminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo-azepine

HRID 54758

Reaktionsgleichung

Reaktionsgleichung von HRID 54758
Cl[CH2:2][C:3]#[N:4].C(N(CC)CC)C.[I-].[Na+].[NH2:14][CH2:15][CH2:16][O:17][CH:18]1[C:24]2[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=2[N:22]([C:30](=[O:49])[C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:46])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[Cl:45])=[CH:33][C:32]=2[O:47][CH3:48])[CH2:21][CH2:20][CH2:19]1>CN(C)C=O.O>[C:3]([CH2:2][NH:14][CH2:15][CH2:16][O:17][CH:18]1[C:24]2[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=2[N:22]([C:30](=[O:49])[C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:46])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[Cl:45])=[CH:33][C:32]=2[O:47][CH3:48])[CH2:21][CH2:20][CH2:19]1)#[N:4]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 189172105-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine

Produkt 1

HCID 537191225-(2-cyanomethylaminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo-azepine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

0.01 ml of chloroacetonitrile, 0.22 ml of triethylamine and 0.24 ml of sodium iodide were added to 50 ml of a solution of 0.7 g of 5-(2-aminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzoazepine dissolved in dimethylformamide. The mixture was stirred at 60° C. for 2 hours. The reaction mixture was mixed with water, followed by extraction with ethyl acetate-n-hexane (10:1). The organic layer was water-washed, dried and subjected to vacuum distilation to remove the solvent. The residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=50/1) and crystallized from acetone-n-hexane to obtain 0.5 g of 5-(2-cyanomethylaminoethoxy)-7-chloro-1-[2-methoxy-4-(2-chlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzo-azepine.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate-n-hexane (10:1)
  2. washwashed
  3. customdried
  4. customsubjected to vacuum distilation
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography (elutant: dichloromethane/methanol=50/1)
  7. customcrystallized from acetone-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1e51edf5b77046b28bfbebbd9e96e5e4
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622947

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