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Methanol → 1-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea

HRID 1505157
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1505157
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[C:5]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:4]=1.ClC(Cl)(O[C:22](=[O:28])OC(Cl)(Cl)Cl)Cl.[N-:30]=[C:31]=O.CO.[CH3:35][N:36]([CH:38]=[O:39])C>CCOC(C)=O>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:38]([NH:36][C:35]2[C:31]3[NH:30][C:22](=[O:28])[NH:10][C:9]=3[CH:6]=[CH:5][CH:4]=2)=[O:39])=[C:5]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 887MethanolHCID 6228DimethylformamideHCID 94429TriphosgeneHCID 105034IsocyanateHCID 58873466HCID 58873466, Verbindung

Produkt 1

HCID 534773861-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea
Ausbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Amine 2b (0.5 ml, 2 mmol) was dissolved in 20 ml of AcOEt and at 0° C. triphosgene (580 mg, 2 mmol) was added to the solution. The mixture was warmed at 80° C. for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1a (296 mg, 1.99 mmol) and the mixture was warmed at 80° C. for 8 hours. (TLC AcOEt 9.5/MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 170 mg of a yellow solid. Yield=20% 1HNMR (DMSO, 400 MHz) δ 1.91 (4H, bs), 3.22 (4H, bs), 4.38 (2H, d, J=5.2 Hz), 6.62 (1H, d, J=8 Hz), 6.72 (1H, t), 6.83 (1H, t), 6.95 (1H, d, J=8 Hz), 7.08 (1H, s), 7.18 (1H, d, J=7.6 Hz), 7.45 (1H, d, J=7.6 Hz), 8.35 (1H, bs), 9.98 (1H, bs), 10.60 (1H, bs); [M+1] 420.18 (C20H20F3N5O2 requires 419.4).

Aufarbeitung

  1. additionwas added to the solution
  2. customthen evaporated
  3. dissolutionthe residue was dissolved in 5 ml of DMF
  4. temperaturethe mixture was warmed at 80° C. for 8 hours
  5. customThe solvent was evaporated
  6. dissolutionthe crude was dissolved in AcOEt (30 ml)
  7. washwashed with water (1×20 ml) and brine
  8. dry with materialThe organic phase was dried over sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe purification of the crude residue by chromatographic column

Quellen und Nachweise

ORD-Eintrag
ord-263a8144649f44bb9e569f3f76882ec5
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09216975B2

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