Imatinib → Imatinib Mesylate

HRID 1404426Notes

Reaction equation

HRID 1404426 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 Mesylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

Imatinib (100 g) was suspended in dimethylsulfoxide (180 ml) and methanesulfonic acid (20 g) was added to mixture at 25 to 30° C. Reaction mass was heated to 45° C. till clear solution and filtered. 10% of filtered solution was added to a mixture of isopropanol (900 ml), ethyl acetate (600 ml) and n-propanol (600 ml) and dimethylsulfoxide (300 ml) at 20° C. followed by seeding and stirred for 30 minutes. Remaining filtered solution was added to above suspension and stirred for 5.0 hours at 20-25° C. Reaction mass was filtered, washed and dried to 102 g of α-form of imatinib mesylate.

Workup

  1. customReaction mass
  2. filtrationfiltered
  3. addition10% of filtered solution was added to a mixture of isopropanol (900 ml), ethyl acetate (600 ml) and n-propanol (600 ml) and dimethylsulfoxide (300 ml) at 20° C.
  4. filtrationRemaining filtered solution
  5. additionwas added to above suspension
  6. stirringstirred for 5.0 hours at 20-25° C
  7. customReaction mass
  8. filtrationwas filtered
  9. washwashed
  10. dry with materialdried to 102 g of α-form of imatinib mesylate

Sources & evidence

ORD record
ord-73b492b3249442138e77e8e984c89b13
Source dataset
uspto-grants-2014_12
Patent number
US08912325B2

Reaction notes

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