Benzylamine → HCID 53629116, Verbindung

HRID 1896367Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896367
[O:1]=[C:2]1[CH2:6][CH:5]([CH2:7][CH2:8][CH3:9])[CH2:4][N:3]1[CH2:10][C:11]1[N:15]([CH2:16][C:17]([OH:19])=O)[CH:14]=[N:13][CH:12]=1.C(N(CC)CC)C.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:27]([NH:34][C:17](=[O:19])[CH2:16][N:15]1[C:11]([CH2:10][N:3]2[CH2:4][CH:5]([CH2:7][CH2:8][CH3:9])[CH2:6][C:2]2=[O:1])=[CH:12][N:13]=[CH:14]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 7504Benzylamine2×HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57743028HCID 57743028, Verbindung

Produkt 1

HCID 53629116HCID 53629116, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a 10 ml, three necked flask fitted with a magnetic stirrer, under inert atmosphere, {5-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]-1H-imidazol-1-yl}acetic acid x50 (0.1 g, 0.33 mmol) is dissolved in DMF (1 ml). Triethylamine (0.1 ml, 0.66 mmol), benzylamine (37 μl, 0.33 mmol) and TBTU (0.16 g, 0.33 mmol) are added and the mixture is stirred for 0.5 h at room temperature. An additional amount of benzylamine (0.0165 mmol) is added and stirring is continued overnight. The solvent is evaporated and the residue is purified by chromatography on silicagel (AcOEt/MeOH/NH4OH: 90/9/1 (v/v/v)). The product is treated with a methanolic solution of HCl and the obtained solid is recrystallized from acetonitrile to afford N-benzyl-2-{5-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]-1H-imidazol-1-yl}acetamide 124.

Aufarbeitung

  1. stirringstirring
  2. waitis continued overnight
  3. customThe solvent is evaporated
  4. customthe residue is purified by chromatography on silicagel (AcOEt/MeOH/NH4OH: 90/9/1 (v/v/v))
  5. additionThe product is treated with a methanolic solution of HCl
  6. customthe obtained solid is recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-104fa6bb934b4449a4ddc106d48783e4
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518943B2

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