Ethanol → HCID 66636856, compound

HRID 1094169Notes

Reaction equation

HRID 1094169 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:33])[C:13](/[CH:23]=[CH:24]/[P:25](=[O:32])([O:29]CC)[O:26]CC)=[CH:14][N:15]3[CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:10][C:9]=2[F:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:35][Si](C)(C)C.C(O)C>C(Cl)(Cl)Cl>[BrH:35].[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:33])[C:13](/[CH:23]=[CH:24]/[P:25](=[O:26])([OH:32])[OH:29])=[CH:14][N:15]3[CH:18]([CH2:19][CH3:20])[CH2:21][CH3:22])=[CH:10][C:9]=2[F:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 86633050HCID 86633050, compound

Product 1

HCID 66636856HCID 66636856, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

200 mg of diethyl {(E)-2-[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]vinyl}phosphonate was dissolved in 2.0 ml of chloroform, and 0.4 ml of bromotrimethylsilane was added, followed by overnight stirring at room temperature. Ethanol was added to the reaction mixture, followed by concentration under a reduced pressure. Ethyl acetate was added to the resulting residue, and the insoluble materials were collected by filtration to obtain 120 mg of {(E)-2-[7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl]vinyl}phosphonic acid hydrobromide.

Workup

  1. concentrationfollowed by concentration under a reduced pressure
  2. additionEthyl acetate was added to the resulting residue
  3. filtrationthe insoluble materials were collected by filtration

Sources & evidence

ORD record
ord-cb7f7c6824b145c395b413c533ec3596
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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