2-Amino-6-nitro-benzoic acid → 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one

HRID 623849

Reaktionsgleichung

Reaktionsgleichung von HRID 623849
N[C:2]1C=CC=C2[C:3]=1C(=O)N(C1CCC(=O)NC1=O)C(C)=N2.[NH2:22][C:23]1[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[C:24]=1[C:25]([OH:27])=[O:26]>C(O)(=O)C>[CH3:2][C:3]1[O:26][C:25](=[O:27])[C:24]2[C:28]([N+:32]([O-:34])=[O:33])=[CH:29][CH:30]=[CH:31][C:23]=2[N:22]=1

Komponenten

4

Edukt 2

HCID 957952-Amino-6-nitro-benzoic acidHCID 24967599Avadomide

Produkt 1

HCID 666429832-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

In yet another embodiment, provided herein is a method for preparing 3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione, or an enantiomer or a mixture of enantiomers thereof or a pharmaceutically acceptable salt, solvate, hydrate, or polymorph thereof; comprising the steps of (a) reacting 2-amino-6-nitrobenzoic acid with an activated acetic acid in a solvent to form 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one; (b) reacting 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one with 3-aminopiperidine-2,6-dione or a salt thereof in a solvent to form 3-(2-methyl-5-nitro-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione; and (c) reducing 3-(2-methyl-5-nitro-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione in a solvent to form 3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione, or an enantiomer or a mixture of enantiomers thereof or a pharmaceutically acceptable salt, solvate, hydrate, or polymorph thereof.

Aufarbeitung

  1. customIn yet another embodiment, provided herein
  2. additionan enantiomer or a mixture of enantiomers

Quellen und Nachweise

ORD-Eintrag
ord-ab7e29518922425b9a462ed560f3b836
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303014B2

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