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

HRID 2177420Notes

Reaction equation

HRID 2177420 reaction equation
[CH3:1][C:2]1O[C:4](=[O:15])[C:5]2[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:16][CH:17]1[CH2:22][CH2:21][C:20](=[O:23])[NH:19][C:18]1=[O:24]>>[CH3:1][C:2]1[N:16]([CH:17]2[CH2:22][CH2:21][C:20](=[O:23])[NH:19][C:18]2=[O:24])[C:4](=[O:15])[C:5]2[C:6](=[CH:8][CH:9]=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[N:7]=1

Participants

3

Reactant 2

HCID 1345083-Amino-2,6-piperidinedioneHCID 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 certain embodiments, the solvent in step (a) (reacting 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one and 3-aminopiperidine-2,6-dione or a salt thereof to form 3-(2-methyl-5-nitro-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione) is acetonitrile. In certain embodiments, the solvent in step (a) is ethyl acetate. In certain embodiments, the solvent in step (a) is a mixture of acetonitrile and ethyl acetate. In certain embodiments, the volume ratio of acetonitrile versus ethyl acetate is ranging from about 0.1 to about 100, from about 0.2 to about 50, from about 0.5 to about 25, from about 1 to about 20, from about 1 to about 10, from about 1 to about 5, or from about 1 to about 2. In certain embodiments, the volume ratio of acetonitrile versus ethyl acetate is ranging from about 0.1 to about 100. In certain embodiments, the volume ratio of acetonitrile versus ethyl acetate is ranging from about 0.2 to about 50. In certain embodiments, the volume ratio of acetonitrile versus ethyl acetate is ranging from about 0.5 to about 25. In certain embodiments, the volume ratio of acetonitrile versus ethyl acetate is ranging from about 1 to about 20. In certain embodiments, the volume ratio of acetonitrile versus ethyl acetate is ranging from about 1 to about 10. In certain embodiments, the volume ratio of acetonitrile versus ethyl acetate is ranging from about 1 to about 5. In certain embodiments, the volume ratio of acetonitrile versus ethyl acetate is ranging from about 1 to about 2. In certain embodiments, the volume ratio of acetonitrile versus ethyl acetate is about 1, about 1.1, about 1.2, about 1.3, about 1.4, about 1.5, about 1.6, about 1.7, about 1.8, about 1.9, or about 2.

Sources & evidence

ORD record
ord-666eeb025c4e464eb5592c6b0516279f
Source dataset
uspto-grants-2015_06
Patent number
US09067912B2

Reaction notes

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