Methanesulfonic Acid → Lurosetron mesylate

HRID 1682505Notes

Reaction equation

HRID 1682505 reaction equation
[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4[N:19]=[CH:20][NH:21][C:22]=4[CH3:23])[C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:24][S:25]([OH:28])(=[O:27])=[O:26]>>[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].[F:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][N:14]([CH2:17][C:18]4[N:19]=[CH:20][NH:21][C:22]=4[CH3:23])[C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6395Methanesulfonic AcidHCID 172999Lurosetron

Product 1

HCID 3037237Lurosetron mesylateYield 76.8%

Conditions

Temperature
4 °C

Procedure

6-Fluoro-2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1-one (224.9 g) was suspended in IMS (1125 ml) and heated to reflux. A solution of methanesulphonic acid (69.2 g) in IMS (675 ml) was added with stirring over 15 minutes. The mixture was subsequently allowed to cool over 3 hours, then seeded and left overnight at ambient temperature before being cooled to 4° C. for 5 hours, with stirring. The mixture was filtered, the solid washed with cold IMS (2×450 ml), and then dried between 40° and 76° C. in vacuo to give the title compound (226 g) as a crystalline solid.

Workup

  1. temperatureheated to reflux
  2. temperatureto cool over 3 hours
  3. waitleft overnight at ambient temperature
  4. stirringwith stirring
  5. filtrationThe mixture was filtered
  6. washthe solid washed with cold IMS (2×450 ml)
  7. customdried between 40° and 76° C. in vacuo

Sources & evidence

ORD record
ord-37b03b4ac557446994013d66bd7ec27f
Source dataset
uspto-grants-1997_06
Patent number
US05635513

Reaction notes

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