Water → Imatinib Mesylate

HRID 1010812Notes

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

Conditions

Temperature: -10 °C

Procedure

Imatinib base (20 g; 0.0405 mole) was suspended in isopropanol (723 ml) and water (24.1 ml) was added. The suspension was cooled to −10° C. Then an isopropanolic-solution of methanesulphonic acid (3.7 g in 19.3 ml of isopropanol; 0.385 mole) was added dropwise into suspension during about 10 minutes. When dosing of methanesulphonic acid was finished the temperature was adjusted at −1° C. and the suspension was stirred about 1 hour and the mixture was placed overnight in a freezer at −28° C. Then, the crystalline product was filtered. The cake was rinsed with MTBE (20 ml) and dried by blowing nitrogen through the filter for 2 hours). Imatinib mesylate Form VIII was obtained (22.90 g; yield: 88.2%).

Workup

customwas adjusted at −1° C.
waitthe mixture was placed overnight in a freezer at −28° C
filtrationThen, the crystalline product was filtered
washThe cake was rinsed with MTBE (20 ml)
customdried
filtrationfilter for 2 hours)

Sources & evidence

ORD record: ord-751fbbd1f16b4163910c98eb8215d85f
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977348B2

Reaction notes

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