Triethylamine → Alosetron

HRID 2379158Notes

Reaction equation

HRID 2379158 reaction equation
CN(C)S([N:6]1[C:10]([CH3:11])=[C:9]([CH2:12][N:13]2[CH2:26][CH2:25][C:16]3[N:17]([CH3:24])[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=4[C:15]=3[C:14]2=[O:27])[N:8]=[CH:7]1)(=O)=O.C(N(CC)CC)C>O1CCOCC1.C(#N)C>[CH3:24][N:17]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:23]=2[C:15]2[C:14](=[O:27])[N:13]([CH2:12][C:9]3[N:8]=[CH:7][NH:6][C:10]=3[CH3:11])[CH2:26][CH2:25][C:16]1=2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 15616320N,N,5-Trimethyl-4-[(2,3,4,5-tetrahydro-5-methyl-1-oxo-1H-pyrido[4,3-b]indol-2-yl)methyl]-1H-imidazole-1-sulphonamide

Product 1

HCID 2099AlosetronYield 69%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N,N,5-trimethyl-4-[(2,3,4,5-tetrahydro-5-methyl-1-oxo-1H-pyrido[4,3-b]indol-2-yl)methyl]-1H-imidazole-1-sulphonamide (401 mg) in a mixture of dioxane (150 ml) and acetonitrile (150 ml) containing triethylamine (1 ml) was irradiated at room temperature with a medium pressure mercury lamp for 24 h. The reaction mixture was then concentrated in vacuo onto FCC silica and purified by FCC eluting with System A (100:8:1) to give the title compound (203 mg) as a solid. The 1H-n.m.r. and t.l.c. data obtained for this material were consistent with those obtained for the product of Example 20.

Workup

  1. customwas irradiated at room temperature with a medium pressure mercury lamp for 24 h
  2. concentrationThe reaction mixture was then concentrated in vacuo onto FCC silica
  3. custompurified by FCC
  4. washeluting with System A (100:8:1)

Sources & evidence

ORD record
ord-94b1eb16f5cb4b95bd60ce0f30dbe5a7
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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