Methanesulfonic Acid → Masitinib mesylate

HRID 1430424Notes

Reaction equation

HRID 1430424 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:36]=[CH:35][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]4[S:25][CH:26]=[C:27]([C:29]5[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=5)[N:28]=4)[CH:17]=3)=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[CH3:37][S:38]([OH:41])(=[O:40])=[O:39]>C(O)C>[CH3:37][S:38]([OH:41])(=[O:40])=[O:39].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([NH:23][C:24]4[S:25][CH:26]=[C:27]([C:29]5[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=5)[N:28]=4)[CH:17]=3)=[O:14])=[CH:35][CH:36]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 100746404-[(4-Methylpiperazin-1-yl)methyl]-N-(4-methyl-3-{[4-(pyridin-3-yl)-1,3-thiazol-2(3H)-ylidene]amino}phenyl)benzamide

Product 1

HCID 25024769Masitinib mesylateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
27.5 °C

Procedure

4-(4-Methyl-piperazin-1-ylmethyl)-N-[4-methyl-3-(4-pyridin-3-yl-thiazol-2-ylamino) -phenyl]-benzamide (1.0 eq) was dissolved in ethanol (4.5 vol) at 65-70° C. Methanesulfonic acid (1.0 eq) was added slowly at the same temperature. The mixture was cooled to 25-30° C. and maintained for 6 h. The product was filtered and dried in a vacuum tray drier at 55-60° C. Yield=85-90%.

Workup

  1. temperaturemaintained for 6 h
  2. filtrationThe product was filtered
  3. customdried in a vacuum tray drier at 55-60° C

Sources & evidence

ORD record
ord-9e75b8a15d8c472b88e6005538c78c78
Source dataset
uspto-grants-2015_01
Patent number
US08940894B2

Reaction notes

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