Water → HCID 86625489, compound

HRID 2263041Notes

Reaction equation

HRID 2263041 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23].O>O1CCCC1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:22](=[O:23])[O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 27633906-(4-Methylpiperazin-1-yl)pyridin-3-amine

Product 1

HCID 86625489HCID 86625489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(4-methylpiperazin-1-yl)pyridine-3-amine (1.00 g, 5.20 mmol) and pyridine (0.509 ml, 6.24 mmol) in tetrahydrofuran (17 ml) was added, under ice-cooling, 2,2,2-trichloroethyl chloroformate (0.509 ml, 6.24 mmol), and the mixture was stirred at room temperature for 1 hour and half. Water was poured to the reaction mixture, and the resulting solution was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Hexane was poured to the residue, and 349 mg (18.2%) of the desired product as a solid was separated by filtration.

Workup

  1. temperaturecooling
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionHexane was poured to the residue, and 349 mg (18.2%) of the desired product as a solid
  7. customwas separated by filtration

Sources & evidence

ORD record
ord-ae7dac89b29c4861b37266d2c16d6a3e
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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