Imatinib → Imatinib Mesylate

HRID 562563Notes

Reaction equation

HRID 562563 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][N:31]3[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]3)=[CH:28][CH:29]=2)=[O:23])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.O1CCOC1.[CH3:43][S:44]([OH:47])(=[O:46])=[O:45]>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][N:31]3[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]3)=[CH:26][CH:25]=2)=[O:23])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.[CH3:43][S:44]([OH:47])(=[O:46])=[O:45]

Participants

5

Reactant 3

HCID 5291ImatinibHCID 6395Methanesulfonic AcidHCID 125861,3-Dioxolane2×

Product 1

HCID 123596Imatinib Mesylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Imatinib base (600 g), 5.7 liters of 1,3-dioxolane and 300 ml of water were added to a vessel. The suspension was stirred at 20° C. for 15 minutes and than 113.3 g of methanesulphonic acid was added. After addition the solution was cooled from 20° C.-10° C. in 1 hour and after 1 hour of stirring the solution was cooled again from 10° C.-5° C. in 1 hour. The suspension was stirred for 4 hours at 5° C. Than 6 liters of dioxolane was added in 30 minutes maintaining the temperature at 5° C. The suspension was left for 2.5 hours at 5° C. without stirring. The suspension was filtered and the product was washed with 6 liters of 1,3-dioxolane.

Workup

  1. additionwas added
  2. additionAfter addition the solution
  3. temperaturewas cooled from 20° C.-10° C. in 1 hour and after 1 hour
  4. temperaturewas cooled again from 10° C.-5° C. in 1 hour
  5. stirringThe suspension was stirred for 4 hours at 5° C
  6. stirringwithout stirring
  7. filtrationThe suspension was filtered
  8. washthe product was washed with 6 liters of 1,3-dioxolane

Sources & evidence

ORD record
ord-3b4e1e39eb274b2eb2005a7bf9a17651
Source dataset
uspto-grants-2011_11
Patent number
US08067421B2

Reaction notes

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