Dimethyl Sulfoxide → {(2RS,6SR)-4-[3-{[(2,4-Dichlorobenzyl)amino]carbonyl}-6-fluoro-8-methoxy-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinolin-7-yl]-2,6-dimethylpiperazin-1-yl}ethanoic acid

HRID 2099323Notes

Reaction equation

HRID 2099323 reaction equation
C([O:3][C:4](=[O:45])[CH2:5][N:6]1[CH:11]([CH3:12])[CH2:10][N:9]([C:13]2[C:22]([O:23][CH3:24])=[C:21]3[C:16]([C:17](=[O:42])[C:18]([C:30]([NH:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=4[Cl:41])=[O:31])=[CH:19][N:20]3[CH2:25][C:26]([F:29])([F:28])[F:27])=[CH:15][C:14]=2[F:43])[CH2:8][CH:7]1[CH3:44])C.[OH-].[Li+].CS(C)=O>O1CCOCC1>[Cl:41][C:35]1[CH:36]=[C:37]([Cl:40])[CH:38]=[CH:39][C:34]=1[CH2:33][NH:32][C:30]([C:18]1[C:17](=[O:42])[C:16]2[C:21](=[C:22]([O:23][CH3:24])[C:13]([N:9]3[CH2:8][CH:7]([CH3:44])[N:6]([CH2:5][C:4]([OH:45])=[O:3])[CH:11]([CH3:12])[CH2:10]3)=[C:14]([F:43])[CH:15]=2)[N:20]([CH2:25][C:26]([F:27])([F:28])[F:29])[CH:19]=1)=[O:31]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 3939Lithium HydroxideHCID 76607269Ethyl{(2RS,6SR)-4-[3-{[(2,4-dichlorobenzyl)amino]carbonyl}-6-fluoro-8-methoxy-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinolin-7-yl]-2,6-dimethylpiperazin-1-yl}ethanoate

Product 1

HCID 73170905{(2RS,6SR)-4-[3-{[(2,4-Dichlorobenzyl)amino]carbonyl}-6-fluoro-8-methoxy-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinolin-7-yl]-2,6-dimethylpiperazin-1-yl}ethanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

45.0 mg (0.06 mmol) of the compound from Example 1 are dissolved in 1 ml of dioxane, and 0.31 ml (0.31 mmol) of a 1M lithium hydroxide solution are subsequently added and the mixture is stirred at room temperature overnight. For the work-up, the solvent is removed on a rotary evaporator, the residue is taken up in water and acidified (pH 3) using 1M hydrochloric acid, and the precipitate formed is dissolved with a little dimethyl sulfoxide. After fine purification via preparative RP-HPLC (method 5), 38 mg of the target compound are obtained from the solution.

Workup

  1. customFor the work-up, the solvent is removed on a rotary evaporator
  2. customthe precipitate formed
  3. customAfter fine purification via preparative RP-HPLC (method 5), 38 mg of the target compound
  4. customare obtained from the solution

Sources & evidence

ORD record
ord-24ba870a1eb647cc93829ba0191431f9
Source dataset
uspto-grants-2009_08
Patent number
US07569563B2

Reaction notes

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