Isopropanol → Imatinib Mesylate

HRID 15376

Reaction equation

HRID 15376 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([NH:26][C:27]([C:29]2[CH:30]=[CH:31][C:32]([CH2:35][N:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)=[CH:33][CH:34]=2)=[O:28])=[CH:11][C:12]=1[NH:13][C:14]1[N:15]=[CH:16][CH:17]=[C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[N:24][CH:25]=2)[N:19]=1.C(O)(C)C.C(OCC)(=O)C>C(O)C>[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][N:36]3[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]3)=[CH:31][CH:30]=2)=[O:28])=[CH:11][C:12]=1[NH:13][C:14]1[N:19]=[C:18]([C:20]2[CH:21]=[CH:22][CH:23]=[N:24][CH:25]=2)[CH:17]=[CH:16][N:15]=1.[CH3:1][S:2]([OH:5])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 5291ImatinibHCID 6395Methanesulfonic AcidHCID 8857Ethyl Acetate

Product 1

HCID 123596Imatinib Mesylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

Methanesulfonic acid (ca. 0.99 eq.) was added, with stirring to a suspension of Imatinib (10.647 g) in ethyl alcohol (173 mL) heated previously to 65° C. and the mixture was stirred for 5 min. The seeds of the α-crystal form (0.279 g) were added to the solution at approx. 44° C. followed by dropwise addition of isopropyl alcohol (65 mL) and ethyl acetate (238 mL). Stirring at room temperature (approx. 24-25° C.) was continued for 4 hours and then the mixture was left without stirring for 64 h. The product was filtered off and washed with 50 mL of ethyl acetate. The crystals were dried under reduced pressure at room temperature to afford 11.85 g (93.1%) of α-crystal form of Imatinib monomesylate.

Workup

  1. additionThe seeds of the α-crystal form (0.279 g) were added to the solution at approx. 44° C.
  2. stirringStirring at room temperature (approx. 24-25° C.)
  3. waitwas continued for 4 hours
  4. waitthe mixture was left
  5. stirringwithout stirring for 64 h
  6. filtrationThe product was filtered off
  7. washwashed with 50 mL of ethyl acetate
  8. customThe crystals were dried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-8b07da66c7b84ae4b6c6d39409d2fcd6
Source dataset
uspto-grants-2010_06
Patent number
US07732601B2

Linked notes

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