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

HRID 1978458Notes

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

Participants

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

extractionthe reaction product was extracted into ethyl acetate
washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
dry with materialdried over Na2SO4
distillationThe solvent was then distilled off under reduced pressure
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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