Triethylamine → HCID 54203560, compound

HRID 2081213Notes

Reaction equation

HRID 2081213 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[Br:8][C:9]1[C:17]2[N:16]([CH3:18])[C:15]3[CH2:19][CH2:20][N:21]([CH2:24][C:25]4[N:26]=[CH:27][NH:28][C:29]=4[CH3:30])[C:22](=[O:23])[C:14]=3[C:13]=2[CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[Br:8][C:9]1[C:17]2[N:16]([CH3:18])[C:15]3[CH2:19][CH2:20][N:21]([CH2:24][C:25]4[N:26]=[CH:27][N:28]([S:3]([N:2]([CH3:7])[CH3:1])(=[O:5])=[O:4])[C:29]=4[CH3:30])[C:22](=[O:23])[C:14]=3[C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 83372Dimethylsulphamoyl chloride2×HCID 15712528HCID 15712528, compound

Product 1

HCID 54203560HCID 54203560, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylsulphamoyl chloride (0.31 ml) was added dropwise to a stirred suspension of 6-bromo-2,3,4,5-tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl) methyl]-1H-pyrido[4,3-b]indol-1-one (1.1 g) and triethylamine (0.48 ml) in dry dichloromethane (100 ml). The mixture was heated at reflux for 18 h, then a further quantity of triethylamine (0.48 ml) and dimethylsulphamoyl chloride (0.31 ml) was added. The solution was heated at reflux for 8 h then left at 21° for ca. 60 h. The solution was concentrated in vacuo and purified by FCC eluting with System A (100:8:1) to give a solid, which was triturated with hexane (50 ml) to give the title compound (500 mg), m.p. 182°-185°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureThe solution was heated
  4. temperatureat reflux for 8 h
  5. concentrationThe solution was concentrated in vacuo
  6. custompurified by FCC
  7. washeluting with System A (100:8:1)
  8. customto give a solid, which
  9. customwas triturated with hexane (50 ml)

Sources & evidence

ORD record
ord-59a616f6b30c4b5ab4f1933511eef21b
Source dataset
uspto-grants-1993_02
Patent number
US05183820

Reaction notes

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