Diisopropylethylamine → N-(5-(8-Naphthalen-1-ylmethyl-4-oxo-1-phenyl-1,3,8,-triazaspiro[-4.5]dec-3-yl)pentyl)guanidine

HRID 651348

Reaktionsgleichung

Reaktionsgleichung von HRID 651348
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[C:10]2([CH2:17][CH2:16][N:15]([CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)[N:9]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:8]1.C(N(C(C)C)CC)(C)C.[N+]([O-])(O)=O.CC1C=C(C)[N:51]([C:55](N)=[NH:56])N=1>CN(C)C=O.O>[C:19]1([CH2:18][N:15]2[CH2:14][CH2:13][C:10]3([N:9]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:8][N:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:55]([NH2:56])=[NH:51])[C:11]3=[O:12])[CH2:17][CH2:16]2)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrate2×HCID 206794343-(5-Aminopentyl)-8-naphthalen-1-ylmethyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

Produkt 1

HCID 178512825N-(5-(8-Naphthalen-1-ylmethyl-4-oxo-1-phenyl-1,3,8,-triazaspiro[-4.5]dec-3-yl)pentyl)guanidineAusbeute 5,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-(5-Aminopentyl)-8-naphthalen-1-ylmethyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one, di-trifluoroacetate (0.137 g, 0.2 mmol) prepared as described in Example 13, was dissolved in dimethylformamide (1 ml) and diisopropylethylamine (0.233 g, 1.8 mmol) and 3,5-dimethylpyrazol-1-carboxamidine nitrate (0.060 g, 0.3 mmol) was added. The mixture was stirred at room temperature for 1 h and the addition of an equal amount 3,5-dimethylpyrazol-1 carboxamidine nitrate was repeated. After stirring for 16 h the mixture was diluted with water (10 ml) and extracted with ether (5×10 ml). The aqueous phase and undissolved syrup were extracted with dichloromethane (10 ml), the dichloromethane solution was washed with water (5×10 ml), dried over MgSO4 and concentrated in vacuo, affording the title compound (0.047 g, 5.2%) as an amorphous powder.

Aufarbeitung

  1. stirringAfter stirring for 16 h the mixture
  2. extractionextracted with ether (5×10 ml)
  3. extractionThe aqueous phase and undissolved syrup were extracted with dichloromethane (10 ml)
  4. washthe dichloromethane solution was washed with water (5×10 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8e43e02b6f0b472cbbea7341b6042c53
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277991B1

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