1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(4-Chlorobenzyl)-4-[4-(5-fluoro-2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl]-1,3,5-triazin-2(1H)-one

HRID 1477709Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1477709
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10](O)=[N:9][C:8]2=[O:14])=[CH:4][CH:3]=1.[N:17]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:21]2C=[CH:23][CH:24]=[CH:25][C:20]=2N=N1.N12CCCN=C1CCCCC2.[F:54][C:55]1[CH:64]=[CH:63][C:58]2[NH:59][C:60](=[S:62])[NH:61][C:57]=2[CH:56]=1>C(#N)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:12]=[N:11][C:10]([N:17]3[CH2:23][CH2:24][CH:25]([N:59]4[C:58]5[CH:63]=[CH:64][C:55]([F:54])=[CH:56][C:57]=5[NH:61][C:60]4=[S:62])[CH2:20][CH2:21]3)=[N:9][C:8]2=[O:14])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724700Benzotriazol-1-yl-oxytripyrrolidinophosphoniumHCID 34348855-Fluoro-1H-benzo[d]imidazole-2(3H)-thioneHCID 178518532HCID 178518532, Verbindung

Produkt 1

HCID 1178391761-(4-Chlorobenzyl)-4-[4-(5-fluoro-2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl]-1,3,5-triazin-2(1H)-oneAusbeute 2,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To an acetonitrile solution (1 mL) of 1-(4-chlorobenzyl)-4-hydroxy-1,3,5-triazin-2(1H)-one (20 mg, 0.08 mmol) synthesized in Reference Synthesis Example 10, (benzotriazol-1-yloxy)tripyrrolidino-phosphonium (47 mg, 0.10 mmol) and 1,8-diazabicyclo[5.4.0]undeca-7-ene (15 μL, 0.10 mmol) were added at room temperature and the resultant mixture was stirred for 20 minutes. To the reaction solution, 5-fluoro-1H-benzo[d]imidazole-2(3H)-thione (25 mg, 0.10 mmol) was added and the resultant reaction solution was stirred at 80° C. for 10 minutes. After the completion of the reaction, the reaction solution was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography (chloroform/ethyl acetate=1/1 (v/v)) to obtain the title compound (0.8 mg, yield: 2.0%).

Aufarbeitung

  1. additionwere added at room temperature
  2. customthe resultant reaction solution
  3. customAfter the completion of the reaction
  4. concentrationthe reaction solution was concentrated under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography (chloroform/ethyl acetate=1/1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-4309dd9c10694831b8bba1f30c6e690b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403798B2

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