3-Amino-2,6-piperidinedione → 3-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione

HRID 623839Notes

Reaction equation

HRID 623839 reaction equation
NC1C=CC=C2C=1C(=O)[N:5]([CH:13]1[CH2:18][CH2:17][C:16](=[O:19])[NH:15][C:14]1=[O:20])C(C)=N2.[CH3:22][C:23]1O[C:25](=[O:36])[C:26]2[C:32]([N+:33]([O-:35])=[O:34])=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=1.NC1CCC(=O)NC1=O>>[CH3:22][C:23]1[N:5]([CH:13]2[CH2:18][CH2:17][C:16](=[O:19])[NH:15][C:14]2=[O:20])[C:25](=[O:36])[C:26]2[C:27](=[CH:29][CH:30]=[CH:31][C:32]=2[N+:33]([O-:35])=[O:34])[N:28]=1

Participants

4

Reactant 3

HCID 1345083-Amino-2,6-piperidinedioneHCID 24967599AvadomideHCID 666429832-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one

Product 1

HCID 666429823-(2-methyl-5-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione

Procedure

In 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-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one with 3-aminopiperidine-2,6-dione or a salt thereof in a solvent in the presence of a coupling reagent to form 3-(2-methyl-5-nitro-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione; and (b) 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.

Workup

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

Sources & evidence

ORD record
ord-5ae0456a47744275ae4e4e08c3e69415
Source dataset
uspto-grants-2016_04
Patent number
US09303014B2

Reaction notes

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