Iodoethane → HCID 9930685, compound

HRID 1266177Notes

Reaction equation

HRID 1266177 reaction equation
[CH:1]1([NH:7][C:8]2[C:9]([F:29])=[CH:10][C:11]3[C:12]([CH:28]=2)=[N:13][C:14]2[N:15]([CH3:27])[CH:16]=[C:17]([C:22]([O:24]CC)=[O:23])[C:18](=[O:21])[C:19]=2[CH:20]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I[CH2:31][CH3:32].[H-].[Na+]>CN(C)C=O>[CH:1]1([N:7]([CH2:31][CH3:32])[C:8]2[C:9]([F:29])=[CH:10][C:11]3[C:12]([CH:28]=2)=[N:13][C:14]2[N:15]([CH3:27])[CH:16]=[C:17]([C:22]([OH:24])=[O:23])[C:18](=[O:21])[C:19]=2[CH:20]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 18549174HCID 18549174, compound

Product 1

HCID 9930685HCID 9930685, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-[(Cyclohexyl)(ethyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was prepared from 0.5 g of ethyl 8-cyclohexylamino-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate, 0.19 cm3 of iodoethane, 0.096 g of sodium hydride as a 60% dispersion in mineral oil and 10 cm3 of dimethylformamide. After treatment with 10 cm3 of water and 2 cm3 of 1N hydrochloric acid, the mixture was extracted 3 times with 20 cm3 of trichloromethane. The combined organic phases were washed 1 time with 20 cm3 of water, dried over magnesium sulphate and concentrated under reduced pressure (20 kPa) at a temperature around 40° C. 0.25 g of 8-[(cyclohexyl)(ethyl)amino]-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid was obtained in the form of a yellow solid melting at about 230° C.

Workup

  1. extractionAfter treatment with 10 cm3 of water and 2 cm3 of 1N hydrochloric acid, the mixture was extracted 3 times with 20 cm3 of trichloromethane
  2. washThe combined organic phases were washed 1 time with 20 cm3 of water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure (20 kPa) at a temperature around 40° C

Sources & evidence

ORD record
ord-e8ef8a828eb043d6bfe6acb49c14fd88
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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