Diketene → HCID 86665949, compound

HRID 1094212Notes

Reaction equation

HRID 1094212 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH:7]1([NH:13][C:14]2[CH:23]=[C:22]3[C:17]([C:18](=[O:35])[C:19]([O:29][CH2:30][C:31](=[N:33][OH:34])[NH2:32])=[CH:20][N:21]3[CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16][C:15]=2[F:36])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C(Cl)(Cl)Cl>[C:4]([O:34][N:33]=[C:31]([NH2:32])[CH2:30][O:29][C:19]1[C:18](=[O:35])[C:17]2[C:22](=[CH:23][C:14]([NH:13][CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]3)=[C:15]([F:36])[CH:16]=2)[N:21]([CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:20]=1)(=[O:5])[CH2:3][C:2]([CH3:1])=[O:6]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 86633068HCID 86633068, compound

Product 1

HCID 86665949HCID 86665949, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

40 μl of diketene was added dropwise under ice-cooling to a 8 ml chloroform solution of 800 mg of 2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}-N′-hydroxyethanimidamide, followed by stirring under ice-cooling for 6 hours. By evaporating the solvent under a reduced pressure, 180 mg of N′-(acetoacetyloxy)-2-{[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]oxy}ethanimidamide was obtained.

Workup

  1. temperaturecooling for 6 hours
  2. customBy evaporating the solvent under a reduced pressure

Sources & evidence

ORD record
ord-aa7bc309501d49fab2f56a9a90446491
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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