Imatinib → Imatinib Mesylate

HRID 562562Notes

Reaction equation

HRID 562562 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]>O1CCOC1>[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 125861,3-DioxolaneSolvent

Procedure

Imatinib base (1 g) was suspended in aqueous 1,3-dioxolane (5 ml, 10% of water, v/v) at 15° C. Methanesulfonic acid (0.125 ml) was added obtaining the solution of imatinib mesylate. The solution thus formed was cool down to about 10° C. and additional portion of 1,3-dioxolane (15 ml) was added into the mixture. The suspension was stirred at 5° C. for 10 min and the white solid was filtered, washed with 1,3-dioxolane, and the solid matter was dried at 25° C. under N2 flow for 4 h to obtain imatinib mesylate Form VI (0.6 g, yield: 50%).

Sources & evidence

ORD record
ord-8d8cd5a48f7040acabc737ac9ea18eb6
Source dataset
uspto-grants-2011_11
Patent number
US08067421B2

Reaction notes

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