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Water → Ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-(1-piperazinyl)nicotinoyl]acetate

HRID 232468
Notes
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Reaction equation

HRID 232468 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[NH:15][C:16]1[N:29]=[C:28](OS(C2C(C)=CC(C)=CC=2C)(=O)=O)[C:27]([F:43])=[CH:26][C:17]=1[C:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:19].C(OCC)(=O)C.O>C(Cl)Cl.CCCCCC>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[NH:15][C:16]1[N:29]=[C:28]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[C:27]([F:43])=[CH:26][C:17]=1[C:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 8857Ethyl AcetateHCID 13849317Ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-(2,4,6-trimethylbenzenesulfonyloxy)nicotinoyl]acetate

Product 1

HCID 13922529Ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-(1-piperazinyl)nicotinoyl]acetateYield 69.9%

Reagents, catalysts & solvents

2
HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

In 2 ml of methylene chloride was dissolved 130 mg of anhydrous piperazine, and 200 mg of ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-(2,4,6-trimethylbenzenesulfonyloxy)nicotinoyl]acetate was added thereto with ice-cooling, after which the resulting mixture was subjected to reaction at the same temperature for 40 minutes. Subsequently, the reaction mixture was added to a mixture of 10 ml of ethyl acetate and 10 ml of water, and the organic layer was separated, washed successively with 2 ml of saturated aqueous sodium hydrogencarbonate solution and 2 ml of saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and to the crystalline material thus obtained was added 1 ml of n-hexane, after which crystals were collected by filtration to obtain 110 mg (yield 69.9%) of ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-(1-piperazinyl)nicotinoyl]acetate. The physical properties of this compound were identical with those of the compound obtained in Example 30.

Workup

  1. additionwas added
  2. temperaturewith ice-cooling
  3. customafter which the resulting mixture was subjected to reaction at the same temperature for 40 minutes
  4. customthe organic layer was separated
  5. washwashed successively with 2 ml of saturated aqueous sodium hydrogencarbonate solution and 2 ml of saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customto the crystalline material thus obtained
  9. filtrationafter which crystals were collected by filtration

Sources & evidence

ORD record
ord-6f9ca15588384edab4dcb97d98ae9697
Source dataset
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04851535

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes