Carbamic acid, 4-pyridinyl-, phenyl ester → 1-(4-((1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)methyl)phenyl)-3-(pyridin-4-yl)urea

HRID 515281Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 515281
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:16])OC2C=CC=CC=2)=[CH:3][CH:2]=1.[NH2:17][C:18]1[CH:47]=[CH:46][C:21]([CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([C:36]([OH:45])([C:41]([F:44])([F:43])[F:42])[C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=3)[CH2:25][CH2:24]2)=[CH:20][CH:19]=1>O1CCOCC1>[F:40][C:37]([F:38])([F:39])[C:36]([C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:26]2[CH2:25][CH2:24][CH:23]([CH2:22][C:21]3[CH:20]=[CH:19][C:18]([NH:17][C:8]([NH:7][C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[O:16])=[CH:47][CH:46]=3)[CH2:28][CH2:27]2)=[CH:35][CH:34]=1)([OH:45])[C:41]([F:44])([F:43])[F:42]

Komponenten

4

Edukt 2

HCID 11401617Carbamic acid, 4-pyridinyl-, phenyl esterHCID 86670937HCID 86670937, Verbindung

Produkt 1

HCID 529190571-(4-((1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)methyl)phenyl)-3-(pyridin-4-yl)ureaAusbeute 26,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Phenyl pyridin-4-ylcarbamate (1.680 mmol, 0.36 g) was added to a stirred solution of 2-(4-((4-(4-aminobenzyl)piperidin-1-yl)methyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (1.120 mmol, 0.5 g) in dioxane (20 mL) and the mixture heated in a microwave for 10 minutes at 130° C. followed by 5 minutes at 130° C. The mixture was washed with water (10 mL) and the organic phase dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by HPLC and concentrated under reduced pressure to afford the title compound (168 mg). MS (ESI) m/z 567.5 [M+H]+

Aufarbeitung

  1. washThe mixture was washed with water (10 mL)
  2. dry with materialthe organic phase dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by HPLC
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dd75a4cf19ab4696ae56c897acbe1636
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

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