Dicyclohexylcarbodiimide → HCID 178495790, Verbindung

HRID 1268908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1268908
[NH2:1][CH2:2][C:3]([C:6]1[NH:7][C:8]([C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[CH2:15][CH2:14]3)[N:10]=1)([CH3:5])[CH3:4].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.Cl.[CH3:53][O:54][CH2:55][CH2:56][N:57]1[CH2:62][CH2:61][CH:60]([C:63](O)=[O:64])[CH2:59][CH2:58]1>CN(C=O)C.ClCCl>[CH3:4][C:3]([C:6]1[NH:10][C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[CH2:15][CH2:14]3)=[C:8]([C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)[N:7]=1)([CH3:5])[CH2:2][NH:1][C:63]([CH:60]1[CH2:59][CH2:58][N:57]([CH2:56][CH2:55][O:54][CH3:53])[CH2:62][CH2:61]1)=[O:64]

Komponenten

7

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 184469145-[2-(2-Amino-1,1-dimethyl-ethyl)-5-pyridin-4-yl-1H-imidazol-4-yl]-indan-1-oneHCID 450750321-(2-Methoxyethyl)piperidine-4-carboxylic acid hydrochloride

Produkt 1

HCID 178495790HCID 178495790, VerbindungAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of the product of Example 1, Step 6 (0.1 g, 0.29 mmol), 1-hydroxybenzotriazole (0.06 g, 0.44 mmol) and polymer bound 1,3-dicyclohexylcarbodiimide (0.4 g, 0.6 mmol, 1.52 mmol/g) in a 1:1 mixture of dichloromethane and DMF (4 ml) was stirred at room temperature for 30 min. A solution of 1-(2-methoxy-ethyl)-piperidine-4-carboxylic acid hydrochloride [WO 97/25309] (0.098 g, 0.44 mmol) in DMF (2 ml) was then added and the mixture stirred at room temperature overnight. The reaction mixture was then filtered, the solvent removed in vacuo and the crude residue purified by silica gel chromatography eluting with a 1:9:90 mixture of 0.88 ammonia solution:methanol:dichloromethane to give the title compound (0.12 g, 80%) as a yellow oil; MS(AP+) m/e 516 [M+H]+.

Aufarbeitung

  1. stirringthe mixture stirred at room temperature overnight
  2. filtrationThe reaction mixture was then filtered
  3. customthe solvent removed in vacuo
  4. customthe crude residue purified by silica gel chromatography
  5. washeluting with a 1:9:90 mixture of 0.88 ammonia solution

Quellen und Nachweise

ORD-Eintrag
ord-9785d6c1b4f84b7da16d686ef341d29b
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199137B2

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