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Sodium Iodide → N-(1-[(thiazol-4-yl)methyl]piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

HRID 1978458
Notes
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Reaction equation

HRID 1978458 reaction equation
Cl[CH2:2][C:3]1[N:4]=[CH:5][S:6][CH:7]=1.Cl.Cl.[NH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:18]([C:20]2[S:30][C:29]3[N:31]4[C:22](=[CH:23][N:24]=[C:25]4[CH:26]=[CH:27][CH:28]=3)[CH:21]=2)=[O:19])[CH2:12][CH2:11]1.C(N(CC)CC)C.[I-].[Na+]>C(O)C.O>[S:6]1[CH:7]=[C:3]([CH2:2][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][NH:17][C:18]([C:20]3[S:30][C:29]4[N:31]5[C:22](=[CH:23][N:24]=[C:25]5[CH:26]=[CH:27][CH:28]=4)[CH:21]=3)=[O:19])[CH2:12][CH2:11]2)[N:4]=[CH:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 27632904-(Chloromethyl)-1,3-thiazoleHCID 21993937N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Product 1

HCID 21993714N-(1-[(thiazol-4-yl)methyl]piperidin-4-ylmethyl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamideYield 36.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 255 mg (1.5 mM) of 4-chloromethylthiazole, 387 mg (1 mM) of N-(piperidin-4-ylmethyl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride, and 697 ml (5 mM) of triethylamine in ethanol (10 ml) was added 225 mg (1.5 mM) of sodium iodide at room temperature and the mixture was refluxed on an oil bath at 90° C. overnight. To this reaction mixture was added water and the reaction product was extracted into ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over Na2SO4. The solvent was then distilled off under reduced pressure and the residue was subjected to silica gel column chromatography. The fractions eluting with ethyl acetate/ethanol/triethylamine (20/20/1) were pooled to provide the title compound as red oil (150 mg).

Workup

  1. extractionthe reaction product was extracted into ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over Na2SO4
  4. distillationThe solvent was then distilled off under reduced pressure
  5. washThe fractions eluting with ethyl acetate/ethanol/triethylamine (20/20/1)

Sources & evidence

ORD record
ord-9f73dde1489d4e02aa3377ed95ae14c3
Source dataset
uspto-grants-2001_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06235731B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes