Benzeneacetic acid, hydrazide → HCID 86613118, compound

HRID 1158638Notes

Reaction equation

HRID 1158638 reaction equation
[Br:1][C:2]1[N:11]=[C:10]([C:12]([NH:14][NH:15]C(=O)CC2C=CC=CC=2)=[O:13])[C:9]([O:25][CH3:26])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.BrC1N=[C:36]([C:38]([OH:40])=O)[C:35](OC)=[C:34]2[C:29]=1[CH:30]=[CH:31][CH:32]=N2.C1(CC(NN)=O)C=CC=CC=1.Cl.CN(C)CCCN=C=NCC>ClCCl.O.ON1C2C=CC=CC=2N=N1>[Br:1][C:2]1[N:11]=[C:10]([C:12]([N:14]([C:38](=[O:40])[CH2:36][C:35]2[CH:34]=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH2:15])=[O:13])[C:9]([O:25][CH3:26])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

7

Reactant 4

HCID 70301Benzeneacetic acid, hydrazideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86613119HCID 86613119, compoundHCID 86613120HCID 86613120, compound

Product 1

HCID 86613118HCID 86613118, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 27960291-Hydroxybenzotriazole hydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Bromo-8-methoxy-N′-(phenylacetyl)[1,6]naphthyridine-7-carbohydrazide. To a solution of 5-bromo-8-methoxy[1,6]naphthyridine-7-carboxylic acid (284 mg, 1.00 mmol) in dichloromethane (25 mL) was added phenylacetic hydrazide (137 mg, 1.00 mmol), 1-hydroxybenzotriazole hydrate (4 mg, 0.0301 mmol), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (212 mg, 1.10 mmol). The reaction mixture was stirred at room temperature for 3 hours, during which time a large amount of white solids formed. The reaction mixture was then partitioned between water and dichloromethane (a large excess of dichloromethane was needed to solubilize product). The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0% to 10% methanol in dichloromethane) to provide 5-bromo-8-methoxy-N-(phenylacetyl)[1,6]naphthyridine-7-carbohydrazide (328 mg, 79%) as a white solid. 1H NMR (DMSO-d6) δ 10.50 (d, J=1.6 Hz, 1H), 10.44 (d, J=1.6 Hz, 1 H), 9.27 (dd, J=4.0, 1.6 Hz, 1H), 8.63 (dd, J=8.8, 1.6 Hz, 1H), 7.94 (dd, J=8.8, 4.0 Hz, 1H), 7.36-7.26 (m, 5 H), 4.16 (s, 3H), 3.57 (s, 2 H); MS m/z 415 (M+1).

Workup

  1. customformed
  2. customThe reaction mixture was then partitioned between water and dichloromethane (a large excess of dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-7ec4c86598754880bfa48c0539b29e9f
Source dataset
uspto-grants-2010_10
Patent number
US07812016B2

Reaction notes

Loading…