Borane;pyridine → N-(1-(4-chloro-3-ethoxybenzyl)piperidin-4-yl)-5-methylnicotinamide

HRID 502358

Reaktionsgleichung

Reaktionsgleichung von HRID 502358
CC1C=NC=C(C=1)C(NC1CCNCC1)=O.ClC1C=CC(C=O)=CC=1OCC.[Cl:29][C:30]1[CH:54]=[CH:53][C:33]([CH2:34][N:35]2[CH2:40][CH2:39][CH:38]([NH:41][C:42]([C:44]3[CH:45]=CC=[C:48]4[C:52]=3[NH:51][CH:50]=[CH:49]4)=[O:43])[CH2:37][CH2:36]2)=[CH:32][C:31]=1[O:55][CH2:56][CH3:57].B.N1C=CC=CC=1>ClCCCl.C(O)(=O)C>[Cl:29][C:30]1[CH:54]=[CH:53][C:33]([CH2:34][N:35]2[CH2:40][CH2:39][CH:38]([NH:41][C:42](=[O:43])[C:44]3[CH:45]=[C:49]([CH3:48])[CH:50]=[N:51][CH:52]=3)[CH2:37][CH2:36]2)=[CH:32][C:31]=1[O:55][CH2:56][CH3:57]

Komponenten

7

Edukt 4

HCID 2723995Borane;pyridineHCID 547756424-Chloro-3-ethoxybenzaldehydeHCID 655621085-Methyl-N-(piperidin-4-yl)-nicotinamideHCID 684568991h-Indole-7-carboxylic acid[1-(4-chloro-3-ethoxy-benzyl)piperidin-4-yl]-amide

Produkt 1

HCID 11963995N-(1-(4-chloro-3-ethoxybenzyl)piperidin-4-yl)-5-methylnicotinamideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 5-methyl-N-(piperidin-4-yl)-nicotinamide (22 mg, 0.10 mmol), 4-chloro-3-ethoxy-benzaldehyde (22 mg, 0.12 mmol) in DCE:EtOH (1:11 mL) was added acetic acid (25 μL) and pyridine-borane complex (25 μL, 8M in pyridine, 0.2 mmol). The reaction was shaken for 16 h, after which time it was concentrated and purified by reversed phase HPLC (MeCN:H2O) affording the title compound (22 mg, 57%). MS: 388.4 (MH+)

Aufarbeitung

  1. concentrationafter which time it was concentrated
  2. custompurified by reversed phase HPLC (MeCN:H2O)

Quellen und Nachweise

ORD-Eintrag
ord-9c544fc82ba740ae82223ec8cd956604
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772253B2

Verknüpfte Notizen

Wird geladen…