Imidazole → 4-{[({[2-(Carbamoylmethyl)phenyl]amino}thioxomethyl)amino]methyl}piperidine carboxylic acid tert-butyl ester

HRID 2110044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110044
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:16]([N:23]1[CH:27]=[CH:26]N=C1)(N1C=CN=C1)=[S:17].N1C=CN=C1.N[C:34]1[CH:39]=[CH:38]C=C[C:35]=1[CH2:40][C:41]([NH2:43])=[O:42]>C(#N)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]([NH:23][C:27]2[CH:26]=[CH:38][CH:39]=[CH:34][C:35]=2[CH2:40][C:41](=[O:42])[NH2:43])=[S:17])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 802641,1'-ThiocarbonyldiimidazoleHCID 2782862-(2-Aminophenyl)acetamideHCID 7368171-Boc-4-(aminomethyl)piperidine

Produkt 1

HCID 866105084-{[({[2-(Carbamoylmethyl)phenyl]amino}thioxomethyl)amino]methyl}piperidine carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

After dissolving 1-N-Boc-4-aminomethylpiperidine (869 mg, 4.06 mmol) in acetonitrile (10 mL), a solution of thiocarbonyldiimidazole (794 mg, 4.46 mmol) and imidazole (82.9 mg, 1.22 mmol) in acetonitrile (15 mL) was added dropwise in an ice bath, and the mixture was stirred at room temperature for 4 hours. After then adding 2-(2-aminophenyl)acetamide (670 mg, 4.46 mmol) thereto, the mixture was stirred overnight at 60° C. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (methylene chloride/methanol=65:1→49:1) to obtain the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (methylene chloride/methanol=65:1→49:1)

Quellen und Nachweise

ORD-Eintrag
ord-221f31db34c942319a3cb7052eb6bed2
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517875B2

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