4-(Dimethylamino)-N-(2-fluoro-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenyl)benzamide → N-(3-(2-Amino-1-(6-morpholino-1H-indol-3-yl)ethyl)-2-fluorophenyl)-4-(dimethylamino)benzamide

HRID 2361354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361354
[CH3:1][N:2]([CH3:39])[C:3]1[CH:38]=[CH:37][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH2:17][N+:18]([O-])=O)[C:11]=2[F:36])=[O:8])=[CH:5][CH:4]=1.[H][H]>CO.[Ni]>[NH2:18][CH2:17][CH:16]([C:12]1[C:11]([F:36])=[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:39])=[CH:38][CH:37]=2)[CH:15]=[CH:14][CH:13]=1)[C:21]1[C:29]2[C:24](=[CH:25][C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:27][CH:28]=2)[NH:23][CH:22]=1

Komponenten

5

Edukt 2

HCID 679949194-(Dimethylamino)-N-(2-fluoro-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenyl)benzamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67994859N-(3-(2-Amino-1-(6-morpholino-1H-indol-3-yl)ethyl)-2-fluorophenyl)-4-(dimethylamino)benzamideAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(dimethylamino)-N-(2-fluoro-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenyl)benzamide (0.388 g, 0.730 mmol) and Raney Ni (a small amount) in MeOH (35 mL) was treated with hydrogen at 55 psi a Parr shaker apparatus for 3 hr. The catalyst was removed by suction filtration. The filtrate was concentrated under vacuum, diluted with CH2Cl2 (100 mL), washed with brine (25 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.321 g, 0.599 mmol, 82% yield) as an off-white solid.

Aufarbeitung

  1. customThe catalyst was removed by suction filtration
  2. concentrationThe filtrate was concentrated under vacuum
  3. additiondiluted with CH2Cl2 (100 mL)
  4. washwashed with brine (25 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customRemoval of solvent under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6beeff3ed10447f38b6f32c46ad9c983
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685969B2

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