Dimethylformamide → N'-(6-oxo-7-phenyl-5,6-dihydro-1,5-naphthyridin-2-yl)propanohydrazide

HRID 42373Notes

Reaction equation

[NH:1]([C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:6]2)[NH2:2].CCN(C(C)C)[CH:23]([CH3:25])[CH3:24].CN(C=[O:33])C>>[O:13]=[C:8]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]2[N:4]=[C:3]([NH:1][NH:2][C:24](=[O:33])[CH2:23][CH3:25])[CH:12]=[CH:11][C:10]=2[NH:9]1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 81531Diisopropylethylamine

HCID 670690086-Hydrazinyl-3-phenyl-1,5-naphthyridin-2(1H)-one

Product 1

HCID 67094058N'-(6-oxo-7-phenyl-5,6-dihydro-1,5-naphthyridin-2-yl)propanohydrazide

Procedure

To a mixture of 6-hydrazino-3-phenyl-1,5-naphthyridin-2(1H)-one (7-2) (70 mg, 0.277 mmol) and DIPEA (0.2 mL, 1.15 mmol) in DMF (3 mL) was stirred at room temperature for 0.5 hours. The solvent was removed under reduced pressure to give N′-(6-oxo-7-phenyl-5,6-dihydro-1,5-naphthyridin-2-yl)propanohydrazide (7-3) as yellow solid.

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-c3a78af3655f4404a3368cd7f41557c9
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536193B2

Reaction notes

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