3-Methylbutanehydrazide → N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-2-(3-methylbutanoyl)hydrazinecarboxamide

HRID 2061187Notes

Reaction equation

HRID 2061187 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([NH:20][C:21]([N:23]3C=CN=C3)=[O:22])[CH:16]=[CH:17][C:18]=2[CH3:19])[C:3]1=[O:28].[CH3:29][CH:30]([CH3:36])[CH2:31][C:32]([NH:34]N)=[O:33]>C1COCC1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([NH:20][C:21]([NH:23][NH:34][C:32](=[O:33])[CH2:31][CH:30]([CH3:36])[CH3:29])=[O:22])[CH:16]=[CH:17][C:18]=2[CH3:19])[C:3]1=[O:28]

Participants

4

Reactant 2

HCID 322833-MethylbutanehydrazideHCID 58368998N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-1H-imidazole-1-carboxamide

Product 1

HCID 66819884N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-2-(3-methylbutanoyl)hydrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 18 (0.08 mmol) was dissolved in THF (0.5 mL) and 3-methylbutanehydrazide (12 mg, 0.1 mmol) was added at rt. The reaction mixture was stirred at rt for 1 h to yield the crude N-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-2-(3-methylbutanoyl)hydrazinecarboxamide 26, which was used without purification after removal of THF. MS m/z 422.2 (M+1).

Sources & evidence

ORD record
ord-c1819de70a614009a444b32353f2bd8d
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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