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

HRID 2177425Notes

Reaction equation

HRID 2177425 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 one specific 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 via transfer hydrogenation 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, wherein steps (a) and (b) are each as described herein elsewhere.

Workup

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

Sources & evidence

ORD record
ord-a03baa313b9a4180a39f5665e9d8e08c
Source dataset
uspto-grants-2015_06
Patent number
US09067912B2

Reaction notes

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