Sodium Hydroxide → Lurosetron

HRID 2081232Notes

Reaction equation

HRID 2081232 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](CCOC)[C:22]=4[CH3:23])[C:15](=[O:16])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.FC1C2N(C)C3CCN(CC4N(COC)C=NC=4C)C(=O)C=3C=2C=CC=1.[OH-].[Na+]>Br>[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 14798Sodium HydroxideHCID 197992486-fluoro-2,3,4,5-tetrahydro-2-[[1-(methoxymethyl)-4-methyl-1H-imidazol-5-yl]methyl]-5-methyl-1H-pyrido[4,3-b]indol-1-oneHCID 197992816-fluoro-2,3,4,5-tetrahydro-2-[[1-(methoxyethyl)-5-methyl-1H-imidazol-4-yl]methyl]-5-methyl-1H-pyrido[4,3-b]indol-1-one

Product 1

HCID 172999Lurosetron

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 6-fluoro-2,3,4,5-tetrahydro-2-[[1-(methoxyethyl)-5-methyl -1H-imidazol-4-yl]methyl]-5-methyl-1H-pyrido[4,3-b]indol-1-one and 6-fluoro-2,3,4,5-tetrahydro-2-[[1-(methoxymethyl)-4-methyl-1H-imidazol-5-yl]methyl]-5-methyl-1H-pyrido[4,3-b]indol-1-one (32 mg) in 47% aqueous hydrobromic acid (4 ml) was heated on a steam bath for ca. 2 h. After cooling, the reaction mixture was added to 2N sodium hydroxide (50 ml) and extracted with ethyl acetate (2×50 ml). The combined, dried organic extracts were adsorbed onto silica and purified by FCC eluting with System A (100:8:1) to give the title compound (6.5 mg), m.p. 229°-232°.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. custompurified by FCC
  4. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-77b4fd6ccb2e47dba56c97af5340df82
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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