Nalidixic Acid → 1-ethyl-7-methyl-4-oxo-N-(2-(pyridin-4-yl)ethyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide

HRID 1290827Notes

Reaction equation

HRID 1290827 reaction equation
[CH3:1][CH2:2][N:3]1[C:9]2[N:10]=[C:11]([CH3:14])[CH:12]=[CH:13][C:8]=2[C:6](=[O:7])[C:5]([C:15]([OH:17])=O)=[CH:4]1.ClCCl.C(OC(Cl)=O)(C)=C.[NH2:28][CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1>C(N(CC)CC)C>[CH2:2]([N:3]1[C:9]2[C:8](=[CH:13][CH:12]=[C:11]([CH3:14])[N:10]=2)[C:6](=[O:7])[C:5]([C:15]([NH:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[O:17])=[CH:4]1)[CH3:1]

Participants

6

Reactant 4

HCID 4421Nalidixic AcidHCID 6344DichloromethaneHCID 832754-PyridineethanamineHCID 93846Isopropenyl chloroformate

Product 1

HCID 99277371-ethyl-7-methyl-4-oxo-N-(2-(pyridin-4-yl)ethyl)-1,4-dihydro-1,8-naphthyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Nalidixic acid (0.45 g) and dichloromethane (20 ml) were combined and cooled to 0° C. under nitrogen. Triethylamine (0.3 ml) was then added, followed by isopropenylchloro-formate (0.24 ml) and the whole stirred for 90 minutes. 4-(2-Aminoethyl)pyridine (0.26 ml) was then added and stirring continued for 20 h, after which time the reaction was concentrated onto silica and purified by flash chromatography to give the title compound as an off white solid.

Workup

  1. stirringstirring
  2. waitcontinued for 20 h
  3. concentrationafter which time the reaction was concentrated onto silica
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-95884ce208fd409b868d63e2a0eea073
Source dataset
uspto-grants-1998_05
Patent number
US05753666

Reaction notes

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