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

HRID 1978545Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1978545
CS(O[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)(=O)=O.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.C(N(CC)CC)C.[I-].[Na+].N12CCCNC1CCCC=C2>C(#N)C>[C:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH2:7][CH2:6][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:14][CH:13]=1)#[N:16]

Komponenten

7

Edukt 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 98128211,8-Diazabicyclo[5.4.0]undec-2-eneHCID 219936463-(4-Cyanophenyl)propyl methanesulfonateHCID 21994154N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride

Produkt 1

HCID 21993829N-[1-[3-(4-cyanophenyl)propan-1-yl]piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-(4-Cyanophenyl)propyl methanesulfonate (307 mg, 1.28 mmol) was added to a stirred solution of N-(piperidin-4-yl)-5-thia-1,8b-diazaacenaphthylene-4-carboxamide dihydrochloride (400 mg, 1.07 mmol), triethylamine (539 mg, 5.33 mmol), sodium iodide (192 mg, 1.28 mmol) and 1,8-diazabicyclo[5.4.0]undecene (326 mg, 2.14 mmol) in acetonitrile (20 ml) at room temperature. After refluxing under nitrogen for 14 hours, the reaction mixture was concentrated in vacuo. The residue was dissolved in water and extracted with chloroform. The extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (20 g) with Ethyl acetate-Methanol (2:1) to give N-[1-[3-(4-cyanophenyl)propan-1-yl]piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide as a purple oil (298 mg, 63%).

Aufarbeitung

  1. temperatureAfter refluxing under nitrogen for 14 hours
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with chloroform
  5. washThe extract was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel (20 g) with Ethyl acetate-Methanol (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f7e7f24fabfc472bb5d7eae155909cd1
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06235731B1

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