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2-Chlorobenzaldehyde → HCID 131716322, Verbindung

HRID 1199985
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1199985
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:18])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.[NH2:28][C:29]([CH3:48])=[CH:30][C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[C:46]2[CH:45]=[CH:44][N:43]=[CH:42][C:41]=2[N:40]=[C:39]1[CH3:47])=[O:32]>C(O)C>[OH2:11].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]1[C:9]([C:8](=[O:18])[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:28][C:29]([CH3:48])=[C:30]1[C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[C:46]2[CH:45]=[CH:44][N:43]=[CH:42][C:41]=2[N:40]=[C:39]1[CH3:47])=[O:32].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]1[C:9]([C:8](=[O:18])[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:28][C:29]([CH3:48])=[C:30]1[C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[C:46]2[CH:45]=[CH:44][N:43]=[CH:42][C:41]=2[N:40]=[C:39]1[CH3:47])=[O:32]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 69962-ChlorobenzaldehydeHCID 2680383-Oxo-3-phenyl-N-pyridin-2-yl-propionamideHCID 70357192HCID 70357192, Verbindung

Produkt 1

HCID 131716322HCID 131716322, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of N-(pyrid-2-yl)-3-phenyl-3-oxopropionamide (0.84 g, 3.5 mM--see Preparation 15), 2-chlorobenzaldehyde (0.49 g, 3.5 mM) and 4-(2-methylimidazo[4,5-c]pyrid-1-yl)butyl 3-aminobut-2-enoate (1.01 g, 3.5 mM--see Preparation 13) in absolute ethanol (20 cm3) was heated at reflux, under nitrogen, for 16 hours. The cooled solution was evaporated to dryness and the residue purified by column chromatography on silica (Merck "Kieselgel 60"--Trade Mark) (2 passes) eluting primarily with ethyl acetate:diethylamine 97:3 and, secondly, dichloromethane: methanol 97:3. The product-containing fractions were evaporated to dryness, the residue re-dissolved in 2 cm3 dichloromethane, and the required solid precipitated by the addition of 25 cm3 ether, yield 0.35 g (16%), m.p. 124°-127°.

Aufarbeitung

  1. temperatureat reflux, under nitrogen, for 16 hours
  2. customThe cooled solution was evaporated to dryness
  3. customthe residue purified by column chromatography on silica (Merck "Kieselgel 60"--Trade Mark) (2 passes)
  4. washeluting primarily with ethyl acetate:diethylamine 97:3
  5. customThe product-containing fractions were evaporated to dryness
  6. dissolutionthe residue re-dissolved in 2 cm3 dichloromethane
  7. customthe required solid precipitated by the addition of 25 cm3 ether, yield 0.35 g (16%), m.p. 124°-127°

Quellen und Nachweise

ORD-Eintrag
ord-acea7259ccad40e2a8f00f5aeaeba4f0
Quelldatensatz
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04904671

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