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

HRID 623844Notes

Reaction equation

HRID 623844 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-one2×

Product 1

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

Procedure

In certain embodiments, the molar ratio of the coupling reagent versus 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one 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 ranging from about 1 to about 10, from about 1 to about 5, or from about 1 to about 3. In certain embodiments, the molar ratio of the coupling reagent versus 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one is ranging from about 1 to about 10. In certain embodiments, the molar ratio of the coupling reagent versus 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one is ranging from about 1 to about 5. In certain embodiments, the molar ratio of the coupling reagent versus 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one is ranging from about 1 to about 3. In certain embodiments, the molar ratio of the coupling reagent versus 2-methyl-5-nitro-4H-benzo[d][1,3]oxazin-4-one is about 1, about 1.5, about 2, about 2.5 or about 3.

Sources & evidence

ORD record
ord-b358f0a544e0472bac0522c73faf64ae
Source dataset
uspto-grants-2016_04
Patent number
US09303014B2

Reaction notes

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