Sodium Iodide → N-[1-[3-(2-methoxycarbonylphenoxy)propan-1-yl]piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide

HRID 1978525Notes

Reaction equation

HRID 1978525 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]([C:12]2[S:22][C:21]3[N:23]4[C:14](=[CH:15][N:16]=[C:17]4[CH:18]=[CH:19][CH:20]=3)[CH:13]=2)=[O:11])[CH2:5][CH2:4]1.C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1.[I-].[Na+].Cl[CH2:45][CH2:46][CH2:47][O:48][C:49]1[CH:58]=[CH:57][CH:56]=[CH:55][C:50]=1[C:51]([O:53][CH3:54])=[O:52]>C(#N)C>[CH3:54][O:53][C:51]([C:50]1[CH:55]=[CH:56][CH:57]=[CH:58][C:49]=1[O:48][CH2:47][CH2:46][CH2:45][N:3]1[CH2:4][CH2:5][CH:6]([NH:9][C:10]([C:12]2[S:22][C:21]3[N:23]4[C:14](=[CH:15][N:16]=[C:17]4[CH:18]=[CH:19][CH:20]=3)[CH:13]=2)=[O:11])[CH2:7][CH2:8]1)=[O:52]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15285144Methyl 2-(3-chloro-1-propoxy)benzoateHCID 21994154N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Product 1

HCID 21993853N-[1-[3-(2-methoxycarbonylphenoxy)propan-1-yl]piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamideYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.80 g (2.14 mmol.) of N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride, 1.5 ml (10.76 mmol.) of triethylamine and 0.65 g (4.27 mmol.) of 1,8-diazabicyclo[5.4.0]unde-7-cene (DBU) in acetonitrile (20 ml) were added, at room temperature, 0.38 g of sodium iodide and 0.59 g (2.58 mmol.) of methyl 2-(3-chloro-1-propoxy)benzoate. The mixture was heated under reflux for 3 days under nitrogen atmosphere. The solvent was distilled off under reduced pressure. To the residue was added water, which was subjected to extraction with chloroform. The organic layer was washed with a saturated aqueous saline solution, which was dried over magnesium sulfate, followed by concentration. The concentrate was purified by means of a column chromatography (methanol/ethyl acetate 30-50%), followed by distilling off the solvent under reduced pressure to afford the object compound (0.81 g, 77%) as a reddish amorphous product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 days under nitrogen atmosphere
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionTo the residue was added water, which
  5. extractionwas subjected to extraction with chloroform
  6. washThe organic layer was washed with a saturated aqueous saline solution, which
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationfollowed by concentration
  9. customThe concentrate was purified by means of a column chromatography (methanol/ethyl acetate 30-50%)
  10. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-02076747396241aa8b92daa15472f96a
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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