Water → HCID 53855063, compound

HRID 246946Notes

Reaction equation

HRID 246946 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:8]1[C:20]([F:21])=[CH:19][C:11]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:10]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[F:30])[N:9]=1.C(Cl)(Cl)Cl.O>C(O)C.CCCCCC>[F:30][C:24]1[CH:25]=[C:26]([F:29])[CH:27]=[CH:28][C:23]=1[NH:22][C:10]1[N:9]=[C:8]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[C:20]([F:21])=[CH:19][C:11]=1[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 6212ChloroformHCID 54122609HCID 54122609, compound

Product 1

HCID 53855063HCID 53855063, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

In 1.5 ml of ethanol was dissolved 140 mg of anhydrous piperazine, and to the resulting solution was added 150 mg of ethyl 2-[6-chloro-2-(2,4-difluorophenylamino)-5-fluoronicotinyl]acetate in portions, and the resulting mixture was subjected to reaction at room temperature for 30 minutes. Subsequently, the reaction mixture was added to a mixture of 5 ml of chloroform and 5 ml of water, and the organic layer was separated, washed successively with 3 ml of water and 3 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 2 ml of n-hexane, after which crystals were collected by filtration to obtain 70 mg (yield 41.2%) of ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-(1-piperazinyl)nicotinyl]acetate

Workup

  1. customthe resulting mixture was subjected to reaction at room temperature for 30 minutes
  2. customthe organic layer was separated
  3. washwashed successively with 3 ml of water and 3 ml of saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customto the crystalline material thus obtained
  7. filtrationafter which crystals were collected by filtration

Sources & evidence

ORD record
ord-18dd54483ec54b8aa6c8ded68dc51780
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

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