Benzamide → Benzamide

HRID 859113Notes

Reaction equation

HRID 859113 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][S:11]([OH:14])(=[O:13])=[O:12]>C(O)C>[CH3:10][S:11]([OH:14])(=[O:13])=[O:12].[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2331BenzamideHCID 6395Methanesulfonic Acid

Product 2

HCID 2331BenzamideHCID 86585690HCID 86585690, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material, 4-(4-methylpiperazin-1-ylmethyl)-N-[4-methyl -3-(4-pyridin-3-yl)pyrimid-in-2-ylamino)phenyl]benzamide methanesulfonate is prepared as follows: 98.6 g (0.2 mol) free 4-(4-methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]benzamide (for preparation see, for example, EP-A-0 564 409) is added to 1.4 l ethanol. To this beige suspension, 19.2 g (0.2 mol) methanesulfonic acid is added dropwise over a period of 20 minutes. The solution is heated under reflux for 20 minutes and then filtered clear at 65° C. The filtrate is evaporated down to 50% and the residue filtered off at 25° C. (filter material A). The mother liquor is evaporated to dryness. This residue and filter material A are suspended in 2.2 l ethanol and dissolved under reflux with the addition of 30 ml water. Cooling overnight to 25°C., filtration, and drying at 65° C. until constancy of weight is achieved result in 4-(4-methylpiperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)phenyl]benzamide as light beige, crystalline mesylate (α-crystal form).

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for 20 minutes
  3. filtrationfiltered clear at 65° C
  4. customThe filtrate is evaporated down to 50%
  5. filtrationthe residue filtered off at 25° C.
  6. filtration(filter material A)
  7. customThe mother liquor is evaporated to dryness
  8. filtrationThis residue and filter material A
  9. dissolutiondissolved
  10. temperatureunder reflux with the addition of 30 ml water
  11. temperatureCooling
  12. filtrationovernight to 25°C., filtration
  13. customdrying at 65° C. until constancy of weight

Sources & evidence

ORD record
ord-ab101788ccd2486bbcf0fa21a05053b1
Source dataset
uspto-grants-2006_12
Patent number
US07151106B2

Reaction notes

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