Water → Imatinib Mesylate

HRID 1010815Notes

Reaction equation

HRID 1010815 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.O.[CH3:39][S:40]([OH:43])(=[O:42])=[O:41]>C(O)(C)C>[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.[CH3:39][S:40]([OH:43])(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 962WaterHCID 5291ImatinibHCID 6395Methanesulfonic Acid

Product 1

HCID 123596Imatinib Mesylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Imatinib base (4 g) was suspended in isopropanol (80 ml) and water (11 ml) at −10° C. Methanesulfonic acid (0.5 ml in 4 ml of isopropanol) was added with stirring and the suspension was stirred for additional 20 min at −5° C. obtaining thus the solution of imatinib mesylate. Then the solution was allowed to crystallize without stirring at −20° C. overnight. The white solid was filtered at −10° C., washed with isopropanol (10 ml) and dried in a stream of nitrogen for 1 h to obtain imatinib mesylate Form XIV (3 g).

Workup

  1. customat −10° C
  2. stirringthe suspension was stirred for additional 20 min at −5° C.

Sources & evidence

ORD record
ord-54162f07cd9e4a99817732ab77f98f7d
Source dataset
uspto-grants-2011_07
Patent number
US07977348B2

Reaction notes

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