Imatinib → Imatinib Mesylate

HRID 1010810Notes

Reaction equation

HRID 1010810 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]>[N+](C)([O-])=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 6375NitromethaneSolvent

Procedure

Imatinib base (1 g) was dissolved in nitromethane (20 ml) at 90° C. and methanesulfonic acid (0.125 ml) was added. The solution thus formed was allowed to crystallise at 10° C. for 5 h. The white solid was filtered, washed with t-butyl methyl ether, and the solid matter was dried in a stream of nitrogen for 4 h to obtain imatinib mesylate Form VII (1.1 g, yield: 93%).

Workup

  1. customThe solution thus formed
  2. customto crystallise at 10° C. for 5 h
  3. filtrationThe white solid was filtered
  4. washwashed with t-butyl methyl ether
  5. customthe solid matter was dried in a stream of nitrogen for 4 h

Sources & evidence

ORD record
ord-2661c9e48cbf465494582125349e4719
Source dataset
uspto-grants-2011_07
Patent number
US07977348B2

Reaction notes

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