Imatinib → Imatinib Mesylate

HRID 1010817Notes

Reaction equation

HRID 1010817 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]>>[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

3

Reactant 2

HCID 5291ImatinibHCID 6395Methanesulfonic Acid

Product 1

HCID 123596Imatinib Mesylate

Conditions

Temperature
10 °C

Procedure

Imatinib base (0.5 g) was dissolved in ethyleneglycoldimethylether (4 ml) at 40° C. and methanesulfonic acid was added (63 μl). The solution was cooled to 10° C. and tert-butyl dimethyl ether was added with stirring. Imatinib mesylate Form α was recovered by filtration, washed with tert-butyl dimethyl ether and dried at 80° C. in a stream of nitrogen. Yield 570 mg (95%).

Workup

  1. filtrationImatinib mesylate Form α was recovered by filtration
  2. washwashed with tert-butyl dimethyl ether
  3. customdried at 80° C. in a stream of nitrogen

Sources & evidence

ORD record
ord-42985521a90b4b8f92eea3488335b128
Source dataset
uspto-grants-2011_07
Patent number
US07977348B2

Reaction notes

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