Hydrochloric Acid → Lurosetron

HRID 2081230Notes

Reaction equation

HRID 2081230 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][N:21](S(N(C)C)(=O)=O)[C:22]=4[CH3:23])[C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>C(O)C>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54505771HCID 54505771, compound

Product 1

HCID 172999LurosetronYield 103.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4-[(6-fluoro-2,3,4,5-tetrahydro-5-methyl-1-oxo-1H-pyrido [4,3-b]indol-2-yl)methyl]-N,N,5-trimethyl-1H-imidazole-1-sulphonamide (92 mg) in absolute ethanol (5 ml) was treated with 2N hydrochloric acid (20 ml) and stirred under nitrogen at 100°-110° for 6 h, and then cooled. 2N Sodium hydroxide (60 ml) was added, and the mixture was extracted with ethyl acetate (2×75 ml). The combined, dried organic extracts were concentrated in vacuo to give a solid (71 mg) which was purified by FCC eluting with System A (100:8:1) to give the title compound (57 mg), m.p. 233°-234°.

Workup

  1. temperaturecooled
  2. extractionthe mixture was extracted with ethyl acetate (2×75 ml)
  3. concentrationdried organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-681a09cb9d1045f0b9294d88381109c6
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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