Triethylamine → HCID 21993854, compound

HRID 1978443Notes

Reaction equation

HRID 1978443 reaction equation
Cl.Cl.[CH3:3][N:4]([CH2:19][CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)[C:5]([C:7]1[S:17][C:16]2[N:18]3[C:9](=[CH:10][N:11]=[C:12]3[CH:13]=[CH:14][CH:15]=2)[CH:8]=1)=[O:6].C(N(CC)CC)C.Br[CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(O)C>[CH3:3][N:4]([CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:34][CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:22][CH2:21]1)[C:5]([C:7]1[S:17][C:16]2[N:18]3[C:9](=[CH:10][N:11]=[C:12]3[CH:13]=[CH:14][CH:15]=2)[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12503(3-Bromopropyl)benzeneHCID 21993798HCID 21993798, compound

Product 1

HCID 21993854HCID 21993854, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 464.3 mg (1.16 mM) of N-methyl-N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride and 0.8 ml (5.74 mM) of triethylamine in ethanol was added 0.21 ml (1.38 mM) of l-bromo-3-phenylpropane at room temperature, and the mixture was refluxed under nitrogen for 15 hours. The solvent was then distilled off under reduced pressure and the residue was diluted with water and extracted with methylene chloride. 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 15 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with methylene chloride
  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-f425e40ecb474ce4ad517d25d595ae49
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

Loading…