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

HRID 1978529Notes

Reaction equation

HRID 1978529 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:10].C(#N)C.Cl.Cl.[NH:19]1[CH2:24][CH2:23][CH:22]([NH:25][C:26]([C:28]2[S:38][C:37]3[N:39]4[C:30](=[CH:31][N:32]=[C:33]4[CH:34]=[CH:35][CH:36]=3)[CH:29]=2)=[O:27])[CH2:21][CH2:20]1.[I-].[Na+]>C(N(CC)CC)C>[C:9]([C:8]1[CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:19]2[CH2:20][CH2:21][CH:22]([NH:25][C:26]([C:28]3[S:38][C:37]4[N:39]5[C:30](=[CH:31][N:32]=[C:33]5[CH:34]=[CH:35][CH:36]=4)[CH:29]=3)=[O:27])[CH2:23][CH2:24]2)[CH:13]=[CH:12][CH:11]=1)#[N:10]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 219940813-(3-Chloropropoxy)benzonitrileHCID 21994154N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Product 1

HCID 21994000N-[1-[3-(3-cyanophenyloxy)propan-1-yl]piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamideYield 57.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

3-(3-Chloropropan-1-yl)oxybenzonitrile (503 mg) was added, at room temperature, to an acetonitrile solution (20 ml) of N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride (800 mg), 1,8b-diazabicyclo[5.4.0]-7-undecene (662 mg), triethylamine (1.09 g) and sodium iodide (285 mg). The mixture was heated under reflux for 6.5 hours under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure. To the concentrate was added water, which was subjected to extraction with chloroform. The extract solution was washed with a saturated aqueous saline solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was purified by means of a silica gel chromatography (ethyl acetate/methanol=2/1) to afford the object compound (565 mg, 57%) as reddish purple crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6.5 hours under nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the concentrate was added water, which
  5. extractionwas subjected to extraction with chloroform
  6. washThe extract solution was washed with a saturated aqueous saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was purified by means of a silica gel chromatography (ethyl acetate/methanol=2/1)

Sources & evidence

ORD record
ord-beb0b1dd9f44477e9310a949873ca747
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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