Piperazine → HCID 22353300, compound

HRID 895490Notes

Reaction equation

HRID 895490 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])[CH:3]=1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(=O)([O-])O.[Na+]>CS(C)=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:5]=[C:4]([NH:15][CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])[CH:3]=[C:2]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:7]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 516892Sodium BicarbonateHCID 22353305HCID 22353305, compound

Product 1

HCID 22353300HCID 22353300, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

N-(2-{[6-Chloro-2-(4-chlorophenyl)pyrimidin-4-yl]amino} ethyl)acetamide (1.00 g) and piperazine (2.66 g) were dissolved in DMSO (40 ml) and sodium hydrogencarbonate added (1.29 g). The mixture was heated to 110° C. for 6 hrs. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (100 ml) and water (100 ml). The aqueous phase was washed further with ethyl acetate (2×100 ml) and the combined organics subsequently washed with saturated brine solution (50 ml), dried over magnesium sulphate, filtered and the solvent removed in vacuo to afford the title compound (1.18 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (100 ml) and water (100 ml)
  3. washThe aqueous phase was washed further with ethyl acetate (2×100 ml)
  4. washthe combined organics subsequently washed with saturated brine solution (50 ml)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6821beaf0ed24bfdaed39f952f322a82
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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