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

HRID 1777242Notes

Reaction equation

HRID 1777242 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-d3713754c4644702893028be24cfb7bf
Source dataset
uspto-grants-2016_02
Patent number
US09266858B2

Reaction notes

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