Triethylamine → (E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-{[methyl-(4-methylcyclohexyl)amino]methyl}phenyl)acrylamide

HRID 735176

Reaktionsgleichung

Reaktionsgleichung von HRID 735176
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15](=[O:30])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[CH:9][CH:8]=1)(=O)=O.[CH3:31][NH:32][CH:33]1[CH2:38][CH2:37][CH:36]([CH3:39])[CH2:35][CH2:34]1.C(N(CC)CC)C>ClCCl>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([C:20]2[CH:19]=[CH:18][C:17]([NH:16][C:15](=[O:30])/[CH:14]=[CH:13]/[C:10]3[CH:11]=[CH:12][C:7]([CH2:6][N:32]([CH3:31])[CH:33]4[CH2:38][CH2:37][CH:36]([CH3:39])[CH2:35][CH2:34]4)=[CH:8][CH:9]=3)=[CH:22][CH:21]=2)=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 4962029N,4-DimethylcyclohexanamineHCID 866018934-[(E)-2-(4'-chlorobiphenyl-4-ylcarbamoyl)vinyl]benzyl Methanesulfonate

Produkt 1

HCID 57845832(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-{[methyl-(4-methylcyclohexyl)amino]methyl}phenyl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A reaction mixture of 100 mg (0.226 mmol) of 4-[(E)-2-(4′-chlorobiphenyl-4-ylcarbamoyl)vinyl]benzyl methanesulfonate, 37.34 mg (0.29 mmol) of methyl-(4-methylcyclohexyl)amine, and 0.1 mL of triethylamine in 10 mL of dichloromethane is stirred for 18 hours at ambient temperature. Then the reaction mixture is extracted between water and dichloromethane, the organic phase is separated off, dried, and evaporated down. The residue is purified by column chromatography on silica gel (eluant: dichloromethane/methanol/ammonia (90:10:1)). Yield: 52 mg (49% of theory); C30H33ClN2O (M=473.05); melting point: 227° C.-258° C.; calc.: molecular ion peak (M+H)+: 473/475 (Cl); found: molecular ion peak (M+H)+: 473/475 (Cl); Rf value: 0.48 (silica gel, dichloromethane/methanol/ammonia (90:10:1)).

Aufarbeitung

  1. extractionThen the reaction mixture is extracted between water and dichloromethane
  2. customthe organic phase is separated off
  3. customdried
  4. customevaporated down
  5. customThe residue is purified by column chromatography on silica gel (eluant: dichloromethane/methanol/ammonia (90:10:1))

Quellen und Nachweise

ORD-Eintrag
ord-578f5fe04aba4cb2a44fce535e45c905
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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