Diisopropylethylamine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-ylsulfanyl]-ethyl}-piperidine-1-carboxylic acid benzyl ester

HRID 1857639Notes

Reaction equation

HRID 1857639 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](OS(C(F)(F)F)(=O)=O)=[C:7]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[CH:14]=3)[C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:29]([O-:31])=[O:30].C(N(C(C)C)CC)(C)C.[CH2:41]([O:48][C:49]([N:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH:52]1[CH2:57][CH2:58][SH:59])=[O:50])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(OCC)(=O)C.O>[CH2:41]([O:48][C:49]([N:51]1[CH2:56][CH2:55][CH2:54][CH2:53][CH:52]1[CH2:57][CH2:58][S:59][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([N+:29]([O-:31])=[O:30])[CH:4]=2)[NH:9][C:8](=[O:12])[C:7]=1[C:13]1[CH:14]=[C:15]([CH3:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)=[O:50])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 54023713Trifluoromethanesulfonic acid 7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yl esterHCID 543726122-(2-Mercaptoethyl)-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 540282832-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-ylsulfanyl]-ethyl}-piperidine-1-carboxylic acid benzyl esterYield 21.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of trifluoromethanesulfonic acid 7-chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yl ester (524 mg in 4 mL dry N,N-dimethylformamide) at 0° C. was added 0.38 mL diisopropylethylamine followed by 2-(2-mercaptoethyl)-piperidine-1-carboxylic acid benzyl ester (455 mg in 1 mL N,N-dimethylformamide) and the reaction allowed to warm to room temperature. After 1 hour, the mixture was diluted with ethyl acetate and water, and the layers separated. The organic portion was washed sequentially with water and brine then dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 7:3) gave the title compound (142 mg).

Workup

  1. customthe layers separated
  2. washThe organic portion was washed sequentially with water and brine
  3. dry with materialthen dried over magnesium sulfate
  4. customPurification of the
  5. concentrationconcentrate by flash chromatography on silica gel (hexane:ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-56977bb378bb455fbaabcc67f416aa63
Source dataset
uspto-grants-2000_11
Patent number
US06147088

Reaction notes

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