Alosetron → 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

HRID 2379148Notes

Reaction equation

HRID 2379148 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[CH3:8][N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:18](=[O:29])[N:19]([CH2:22][C:23]3[N:24]=[CH:25][NH:26][C:27]=3[CH3:28])[CH2:20][CH2:21][C:10]1=2.C(N(CC)CC)C>ClCCl>[CH3:1][N:2]([CH3:7])[S:3]([N:26]1[C:27]([CH3:28])=[C:23]([CH2:22][N:19]2[CH2:20][CH2:21][C:10]3[N:9]([CH3:8])[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:11]=3[C:18]2=[O:29])[N:24]=[CH:25]1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 2099AlosetronHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of dimethylsulphamoyl chloride (0.107 ml) in dry dichloromethane was added to a stirred solution of 2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1-one (0.294 g) and triethylamine (0.2 ml) in dry dichloromethane (30 ml) under nitrogen, and the mixture was heated at reflux for ca. 24 h. After cooling the solution was concentrated onto FCC silica and purified by FCC eluting with System A (150:8:1) to give an oil. This oil was triturated with ether to give a solid which was further purified by slow evaporation from a solution in ethyl acetate to give the title compound (122 mg), m.p. 194°-196°, t.l.c. (System A, 100:8:1) Rf 0.43.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for ca. 24 h
  3. temperatureAfter cooling the solution
  4. concentrationwas concentrated onto FCC silica
  5. custompurified by FCC
  6. washeluting with System A (150:8:1)
  7. customto give an oil
  8. customThis oil was triturated with ether
  9. customto give a solid which
  10. customwas further purified by slow evaporation from a solution in ethyl acetate

Sources & evidence

ORD record
ord-53b859689d8e4bf6adffee68d79c424f
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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