Triethylamine → HCID 21993602, compound

HRID 1978448Notes

Reaction equation

HRID 1978448 reaction equation
Cl.Cl.Cl.[N:4]1([CH2:10][CH2:11][NH:12][C:13]([C:15]2[S:25][C:24]3[N:26]4[C:17](=[CH:18][N:19]=[C:20]4[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)=[O:14])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.C(N(CC)CC)C.Br[CH2:35][CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(O)C>[C:38]1([CH2:37][CH2:36][CH2:35][N:7]2[CH2:8][CH2:9][N:4]([CH2:10][CH2:11][NH:12][C:13]([C:15]3[S:25][C:24]4[N:26]5[C:17](=[CH:18][N:19]=[C:20]5[CH:21]=[CH:22][CH:23]=4)[CH:16]=3)=[O:14])[CH2:5][CH2:6]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12503(3-Bromopropyl)benzeneHCID 21993876HCID 21993876, compound

Product 1

HCID 21993602HCID 21993602, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.63 g (3.71 mM) of N-[2-(1-piperazinyl)ethan-1-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide trihydrochloride and 3.0 ml (21.5 mM) of triethylamine in ethanol (16 ml) was added 0.68 ml (4.47 mM) of 1-bromo-3-phenylpropane at room temperature, and the mixture was refluxed under nitrogen for 20 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with chloroform. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over MgSO4, and purified by column chromatography (methanol/ethyl acetate 20-50%) to provide the title compound.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 20 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over MgSO4
  7. custompurified by column chromatography (methanol/ethyl acetate 20-50%)

Sources & evidence

ORD record
ord-a58423fe202047e8a94ca2c856b938fc
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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