Potassium Iodide → Ethyl{(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

HRID 2099319Notes

Reaction equation

HRID 2099319 reaction equation
Cl.[Cl:2][C:3]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([O:29][CH3:30])[C:14]([N:21]3[CH2:26][CH:25]([CH3:27])[NH:24][CH:23]([CH3:28])[CH2:22]3)=[C:15]([F:20])[CH:16]=2)[N:11]([CH2:31][C:32]([F:35])([F:34])[F:33])[CH:10]=1)=[O:8].Cl[CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:46]([O:45][C:43](=[O:44])[CH2:42][N:24]1[CH:23]([CH3:28])[CH2:22][N:21]([C:14]2[C:13]([O:29][CH3:30])=[C:12]3[C:17]([C:18](=[O:19])[C:9]([C:7]([NH:6][CH2:5][C:4]4[CH:36]=[CH:37][C:38]([Cl:40])=[CH:39][C:3]=4[Cl:2])=[O:8])=[CH:10][N:11]3[CH2:31][C:32]([F:34])([F:35])[F:33])=[CH:16][C:15]=2[F:20])[CH2:26][CH:25]1[CH3:27])[CH3:47]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 86623862N-(2,4-Dichlorobenzyl)-7-[(3RS,5RS)-3,5-dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-1-(2,2,2-trifluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide hydrochloride

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

810.0 mg (1.29 mmol) of N-(2,4-dichlorobenzyl)-7-[(3RS,5SR)-3,5-dimethylpiperazin-1-yl]-6-fluoro-8-methoxy-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinoline-3-carboxamide hydrochloride (Example 38A), 396.5 mg (3.24 mmol) of ethyl chloroacetate, 64.5 mg (0.39 mmol) of potassium iodide and 804.9 mg (5.82 mmol) of potassium carbonate are stirred under reflux in 20 ml of acetonitrile overnight. The Work-up takes place in analogy to the general working instructions 1, and after purification via preparative RP-HPLC (method 5) 1050 mg of the target compound are obtained.

Workup

  1. customafter purification via preparative RP-HPLC (method 5) 1050 mg of the target compound
  2. customare obtained

Sources & evidence

ORD record
ord-1a8901b900474ae392c580a53e80e00c
Source dataset
uspto-grants-2009_08
Patent number
US07569563B2

Reaction notes

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