Imatinib → Imatinib Mesylate

HRID 1404424Notes

Reaction equation

HRID 1404424 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]>O1CCCC1.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

5

Reactant 2

HCID 5291ImatinibHCID 6395Methanesulfonic Acid

Product 1

HCID 123596Imatinib Mesylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of imatinib (5 g) in tetrahydrofuran (20 ml) and water (10 ml), methanesulphonic acid (0.97 gl) was added to get clear solution. Reaction mixture was charcoalised and filtered. Tetrahydrofuran (75 ml) was added slowly to the reaction mixture at 25-30° C. The resulting mixture was filtered, washed with t-butylmethyl ether and dried to give 5.2 g of the title compound having purity 99.68% by HPLC.

Workup

  1. additionwas added
  2. customto get clear solution
  3. customReaction mixture
  4. filtrationfiltered
  5. additionTetrahydrofuran (75 ml) was added slowly to the reaction mixture at 25-30° C
  6. filtrationThe resulting mixture was filtered
  7. washwashed with t-butylmethyl ether
  8. customdried

Sources & evidence

ORD record
ord-29c511bd91b842828cdeaef7b48e9801
Source dataset
uspto-grants-2014_12
Patent number
US08912325B2

Reaction notes

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