Triethylamine → N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(4-benzyl-piperazin-1-yl)-benzamide

HRID 478633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 478633
[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH2:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2].Cl.C[CH:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)[CH3:17].[CH:33]1[CH:34]=[CH:35]C2N(O)N=N[C:37]=2[CH:38]=1.C(N(CC)CC)C>CN(C=O)C>[C:1]([CH2:3][NH:4][C:5]([C:7]1([NH:13][C:28](=[O:30])[C:27]2[CH:26]=[CH:25][C:24]([N:21]3[CH2:20][CH2:19][N:18]([CH2:16][C:17]4[CH:35]=[CH:34][CH:33]=[CH:38][CH:37]=4)[CH2:23][CH2:22]3)=[CH:32][CH:31]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6])#[N:2]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 111946841-Amino-cyclohexanecarboxylic acid cyanomethyl amideHCID 470022034-(4-(Propan-2-yl)piperazin-1-yl)benzoic acid hydrochloride

Produkt 1

HCID 10276295N-[1-(Cyanomethyl-carbamoyl)-cyclohexyl]-4-(4-benzyl-piperazin-1-yl)-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-Amino-cyclohexanecarboxylic acid cyanomethyl-amide (0.84 mmol), 4-[4-(2-propyl)-piperazin-1-yl]-benzoic acid hydrochloride (0.84 mmol), HOBT (0.84 mmol), WSCD (0.84 mmol) and triethylamine (0.84 mmol) are dissolved in DMF (2 ml) and stirred overnight at rt. After evaporation of the solvent, the residue is dissolved in a mixture of water and sodium carbonate (to ensure slightly basic conditions) and extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. The residue is suspended in methanol and the solid filtered of and dried (vacuum). A pale powder with mp. 210-212° C., Rf=0.20 (CH2Cl2/MeOH=95:5) is obtained.

Aufarbeitung

  1. customAfter evaporation of the solvent
  2. dissolutionthe residue is dissolved in a mixture of water and sodium carbonate (
  3. extractionextracted three times with ethyl acetate
  4. extractionThe combined extract
  5. dry with materialis dried over sodium sulfate
  6. customevaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)
  9. customA pale powder with mp. 210-212° C., Rf=0.20 (CH2Cl2/MeOH=95:5) is obtained

Quellen und Nachweise

ORD-Eintrag
ord-50853463da694ce2b86802ac58ded36b
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642239B2

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