Trifluoroacetic acid → (4,4-Difluoro-piperidin-1-yl)-[5-(piperidin-4-yloxy)-1H-indol-2-yl]-methanone

HRID 19894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19894
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][C:26]([C:31]([N:33]2[CH2:38][CH2:37][C:36]([F:40])([F:39])[CH2:35][CH2:34]2)=[O:32])=[CH:25]3)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[F:40][C:36]1([F:39])[CH2:37][CH2:38][N:33]([C:31]([C:26]2[NH:27][C:28]3[C:24]([CH:25]=2)=[CH:23][C:22]([O:21][CH:18]2[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]2)=[CH:30][CH:29]=3)=[O:32])[CH2:34][CH2:35]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 670179124-[2-(4,4-Difluoro-piperidine-1-carbonyl)-1H-indol-5-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 67017913(4,4-Difluoro-piperidin-1-yl)-[5-(piperidin-4-yloxy)-1H-indol-2-yl]-methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (4.13 mL, 10.0 eq.) was added to a cold (0° C.) solution of 4-[2-(4,4-difluoro-piperidine-1-carbonyl)-1H-indol-5-yloxy]-piperidine-1-carboxylic acid tert-butyl ester (example 43, step 5, 2.5 g, 1.0 eq.) in dichloromethane (20 mL). The mixture was stirred for 1 h at room temperature, evaporated to dryness and purified on silica gel, eluting with dichloromethane/methanol/ammonium hydroxide 95:5:0.25, to yield 1.7 g (86%) from the desired product as white solid. MS (m/e): 364.4 (MH+, 100%).

Aufarbeitung

  1. customevaporated to dryness
  2. custompurified on silica gel
  3. washeluting with dichloromethane/methanol/ammonium hydroxide 95:5:0.25

Quellen und Nachweise

ORD-Eintrag
ord-b0ee83c0be54415d87215529c963235c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745479B2

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