5-(4-Methyl-3-nitrobenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide → 5-(3-Amino-4-methylbenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

HRID 512530

Reaktionsgleichung

Reaktionsgleichung von HRID 512530
[CH3:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[S:13][C:12]([NH:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)=[N:11][C:10]=2[C:25]([NH2:27])=[O:26])=[O:7])=[CH:4][C:3]=1[N+:30]([O-])=O>CO.C1COCC1.[Pd]>[NH2:30][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:2]=1[CH3:1])[C:6]([NH:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[N:11][C:10]=1[C:25]([NH2:27])=[O:26])=[O:7]

Komponenten

4

Edukt 1

HCID 867033715-(4-Methyl-3-nitrobenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

Produkt 1

HCID 725504095-(3-Amino-4-methylbenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamideAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 5-(4-methyl-3-nitrobenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide (0.07 g, 0.15 mmol) in MeOH-THF (10 mL, 1:1) was added 10% Pd/C (0.014 g) under N2-atmosphere. The mixture was stirred for 16 hrs under hydrogen atmosphere. The insoluble material was then filtered off, and the filtrate was concentrated under reduced pressure to give 0.032 g (49% yield) of the titled compound.

Aufarbeitung

  1. filtrationThe insoluble material was then filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-259df8815fd241989c8d8e9d21a62a95
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102637B2

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