Methanol → HCID 86633068, compound

HRID 1094211Notes

Reaction equation

HRID 1094211 reaction equation
CO.[CH:3]1([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:29])[C:15]([O:25][CH2:26][C:27]#[N:28])=[CH:16][N:17]3[CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:12][C:11]=2[F:30])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Cl.[NH2:32][OH:33]>C(N(CC)CC)C>[CH:3]1([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14](=[O:29])[C:15]([O:25][CH2:26][C:27](=[N:32][OH:33])[NH2:28])=[CH:16][N:17]3[CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[CH:12][C:11]=2[F:30])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 66636991HCID 66636991, compound

Product 1

HCID 86633068HCID 86633068, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a 30 ml methanol solution of 1.5 g of {[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}acetonitrile were added 1.1 ml of triethylamine and 540 mg of hydroxylamine hydrochloride, followed by heating under reflux for 27 hours. The solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 850 mg of 2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}-N′-hydroxyethanimidamide.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 27 hours
  3. customThe solvent was evaporated under a reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40f722224cff4b82a754f2330888840a
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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