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Piperidin-4-ol → 1-(4-(4-Bromophenylsulfonyl)phenyl)-3-(3-((4-hydroxypiperidin-1-yl)(imino)methyl)phenyl)urea

HRID 1797935
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1797935
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=3)=[O:19])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(C1C=C(NC(=O)N)C=CC=1)#N.[NH:41]1[CH2:46][CH2:45][CH:44]([OH:47])[CH2:43][CH2:42]1>Cl.O1CCOCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([N:41]4[CH2:46][CH2:45][CH:44]([OH:47])[CH2:43][CH2:42]4)=[NH:28])[CH:22]=3)=[O:19])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1
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Komponenten

6

Edukt 3

HCID 79341Piperidin-4-olHCID 206364711-(3-Cyanophenyl)ureaHCID 57504036HCID 57504036, Verbindung

Produkt 1

HCID 575040281-(4-(4-Bromophenylsulfonyl)phenyl)-3-(3-((4-hydroxypiperidin-1-yl)(imino)methyl)phenyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel
HCID 21966525
Dioxane Methanol
Lösungsmittel

Versuchsvorschrift

Under argon atmosphere, 1 equivalent of 1-(4-(4-bromophenylsulfonyl)phenyl)-3-(3-cyanophenyl)urea (VIII) [or a correspondent 14444-substituted-phenylsulfonyl)phenyl)-3-(3-cyanophenyl)urea] was dissolved in of 4 M HCl in dioxane/MeOH 5:1. The solution was stirred overnight at rt then the solvent was removed in vacuo. The residue was washed with diethylether, dried in vacuo, dissolved in dry MeOH (or DMF) and reacted with 1.1 to 2 equivalents of piperidin-4-ol (or 1.1 to 2 equivalents of the corresponding secondary amine) at temperature between 55 and 70° C. for a minimum of 4 h to a maximum of 22 h. The products were purified either by flash chromatography, using a silica gel column and an appropriate gradient of MeOH in DCM as eluent, or by preparative HPLC, using a reverse-phase column and a gradient of acetonitrile in 0.1% HCOOHaq.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. washThe residue was washed with diethylether
  3. customdried in vacuo
  4. dissolutiondissolved in dry MeOH (or DMF)
  5. customThe products were purified either by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-26a1059800b6428da30c7c35f22aad99
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08343963B2

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