Imatinib → Imatinib Mesylate

HRID 1404425Notes

Reaction equation

HRID 1404425 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.[CH3:38][S:39]([OH:42])(=[O:41])=[O:40]>CS(C)=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.[CH3:38][S:39]([OH:42])(=[O:41])=[O:40]

Participants

4

Reactant 2

HCID 5291ImatinibHCID 6395Methanesulfonic Acid

Product 1

HCID 123596Imatinib MesylateYield 82%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of imatinib (10 g) in dimethylsulfoxide (50 ml), methanesulfonic acid (2 g) was added at ambient temperature and reaction mixture was heated to 45° C. to get clear solution. Reaction mixture was filtered. 10-15% of resulting filtered solution was added to isopropanol (210 ml) at 55-60° C. and stirred for 15 minutes. Seeding of α-form (0.2 g) was added to this solution followed by the addition of remaining filtered solution and mixture was stirred for 2.0 hours at 55 to 60° C. The reaction mass was cooled to 20-25° C. and stirred for another 2 hours at 20 to 25° C. Reaction mass was filtered, washed and dried to give 9.8 g of title compound having DSC: 226° C.

Workup

  1. additionwas added at ambient temperature
  2. customreaction mixture
  3. customto get clear solution
  4. customReaction mixture
  5. filtrationwas filtered
  6. custom10-15% of resulting
  7. filtrationfiltered solution
  8. additionwas added to isopropanol (210 ml) at 55-60° C.
  9. additionSeeding of α-form (0.2 g) was added to this solution
  10. additionfollowed by the addition
  11. filtrationof remaining filtered solution and mixture
  12. stirringwas stirred for 2.0 hours at 55 to 60° C
  13. temperatureThe reaction mass was cooled to 20-25° C.
  14. stirringstirred for another 2 hours at 20 to 25° C
  15. customReaction mass
  16. filtrationwas filtered
  17. washwashed
  18. customdried

Sources & evidence

ORD record
ord-2f8b57f2f6fe431c921293ee0d3e78a5
Source dataset
uspto-grants-2014_12
Patent number
US08912325B2

Reaction notes

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