Isopropanol → Imatinib Mesylate

HRID 1010804Notes

Reaction equation

HRID 1010804 reaction equation
C(O)(C)C.[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([NH:25][C:26]([C:28]2[CH:29]=[CH:30][C:31]([CH2:34][N:35]3[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]3)=[CH:32][CH:33]=2)=[O:27])=[CH:10][C:11]=1[NH:12][C:13]1[N:14]=[CH:15][CH:16]=[C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[N:23][CH:24]=2)[N:18]=1.[CH3:42][S:43]([OH:46])(=[O:45])=[O:44]>O>[CH3:5][C:6]1[CH:7]=[CH:8][C:9]([NH:25][C:26]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][N:35]3[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]3)=[CH:30][CH:29]=2)=[O:27])=[CH:10][C:11]=1[NH:12][C:13]1[N:14]=[CH:15][CH:16]=[C:17]([C:19]2[CH:20]=[CH:21][CH:22]=[N:23][CH:24]=2)[N:18]=1.[CH3:42][S:43]([OH:46])(=[O:45])=[O:44]

Participants

5

Reactant 3

HCID 3776Isopropanol2×HCID 5291ImatinibHCID 6395Methanesulfonic Acid

Product 1

HCID 123596Imatinib Mesylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of imatinib mesylate and isopropanol is prepared by a process comprising: providing a suspension of imatinib base and isopropanol containing up to 7% by weight of water; admixing the suspension with cooled methanesulfonic acid; and maintaining the mixture at the cooled temperature to obtain a solution of imatinib mesylate. Preferably, the suspension of imatinib base is prepared by suspending imatinib base in isopropanol containing up to 7% by weight of water at a temperature of about −10° C. to about −5° C., more preferably, at a temperature of about −10° C. Preferably, the isopropanol contains up to 5% of water by weight. Preferably, methanesulfonic acid is added to the suspension at a temperature of about 0° C. to about −10° C., more preferably at a temperature of about −10° C., most preferably in a stoichiometric amount. Preferably, the solution is maintained at a temperature of about 0° C. to about −20° C., more preferably, at a temperature of about −15° C. Preferably, the solution is maintained for a period of about 10 hours to about 24 hours, more preferably for about 12 hours to about 16 hours, most preferably about 12 hours.

Workup

  1. customproviding
  2. temperatureand maintaining the mixture at the cooled temperature

Sources & evidence

ORD record
ord-c11052d27c9145bdb2aa9b946965dbee
Source dataset
uspto-grants-2011_07
Patent number
US07977348B2

Reaction notes

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