Diisopropylethylamine → 2-{(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-piperazin-4-yl}-ethanal O-[2-(morpholin-4-yl)ethyl]oxime

HRID 10167

Reaktionsgleichung

Reaktionsgleichung von HRID 10167
[N:1]1([CH2:7][CH2:8][O:9][N:10]=[CH:11][CH2:12]Cl)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:14][C:15]([F:45])([F:44])[C:16]1[CH:17]=[C:18]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[C:19]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][C@H:22]1[CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=[O:20].C(N(C(C)C)CC)(C)C>C(#N)C>[N:1]1([CH2:7][CH2:8][O:9][N:10]=[CH:11][CH2:12][N:24]2[CH2:25][CH2:26][N:21]([C:19](=[O:20])[C:18]3[CH:17]=[C:16]([C:15]([F:14])([F:45])[F:44])[CH:39]=[C:38]([C:40]([F:42])([F:43])[F:41])[CH:37]=3)[C@H:22]([CH2:27][C:28]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[NH:30][CH:29]=3)[CH2:23]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazineHCID 738572932-chloroethanal O-[2-(morpholin-4-yl)ethyl]oxime

Produkt 1

HCID 867601842-{(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-piperazin-4-yl}-ethanal O-[2-(morpholin-4-yl)ethyl]oximeAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-chloroethanal O-[2-(morpholin-4-yl)ethyl]oxime (0.13 g), (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(1H-indol-3-ylmethyl)piperazine (0.29 g), diisopropylethylamine (0.11 mL), and acetonitrile (10 mL) was heated under reflux overnight. After cooling to room temperature the solvent was removed in vacuo, and the residue treated with dichloromethane and K2CO3 (aq). The layers were separated, the organic layer was dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 92/7.5/0.5) to afford 2-{(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)-piperazin-4-yl}-ethanal O-[2-(morpholin-4-yl)ethyl]oxime 0.38 g (95%) as an E/Z mixture. MH+ 626, Rf 0.53+0.66 (E+Z isomer) (CH2Cl2/MeOH/NH4OH 92/7.5/0.5).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customwas removed in vacuo
  4. additionthe residue treated with dichloromethane and K2CO3 (aq)
  5. customThe layers were separated
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (SiO2, CH2Cl2/MeOH/NH4OH 92/7.5/0.5)

Quellen und Nachweise

ORD-Eintrag
ord-ae023882c9984179bbf5210487a49852
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094779B2

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