Imatinib → Imatinib Mesylate

HRID 889578Notes

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

Reactant 2

HCID 5291Imatinib

HCID 6395Methanesulfonic Acid

Product 1

HCID 123596Imatinib Mesylate

Procedure

In another embodiment, the invention encompasses processes for preparing imatinib mesylate comprising: (a) condensing N-(2-methyl-5-aminophenyl-4-(3-pyridyl)-2-pyrimidine-amine and 4-(4-methylpiperazin-1-yl-methyl)benzoyl chloride dihydrochloride in the presence of a solvent to obtain imatinib hydrochloride; (b) combining the imatinib hydrochloride with a base to obtain imatinib base; and (c) combining the imatinib base with methanesulfonic acid to obtain imatinib mesylate, wherein the solvent is not an organic solvent.

Sources & evidence

ORD record: ord-4298f591442745aeb92dd132d3fd2c56
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252926B2

Reaction notes

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