p-Toluenesulfonic acid → 2-Chloro-5-[[[3-[(1-methylethyl)amino]propyl]amino]methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1593828

Reaktionsgleichung

Reaktionsgleichung von HRID 1593828
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[CH:24]([NH:27][CH2:28][CH2:29][CH2:30][NH2:31])([CH3:26])[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][NH:31][CH2:30][CH2:29][CH2:28][NH:27][CH:24]([CH3:26])[CH3:25])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2)=[O:5]

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 76888N-Isopropylpropane-1,3-diamineHCID 120853462-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide

Produkt 1

HCID 101136262-Chloro-5-[[[3-[(1-methylethyl)amino]propyl]amino]methyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideAusbeute 4,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 2-chloro-5-formyl-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.244 g, Example 25b), N-isopropyl-1,3-propanediamine (0.211 g), p-toluenesulfonic acid (0.005 g) and toluene (30 ml) were refluxed together under Dean-Stark conditions for 3 h. The mixture was cooled and concentrated under reduced pressure to an oil. This was dissolved in ethanol (30 ml) and cooled to 0° C. under a nitrogen atmosphere. Solid sodium borohydride (0.040 g) was added portionwise and the mixture stirred at room temperature for 30 min, then concentrated under reduced pressure and the residue purified by column chromatography over silica (eluting with 9:1:0.1 dichloromethane/methanol/35% aqueous ammonia) to give the title compound (0.015 g) and a by-product (see Example 27).

Aufarbeitung

  1. temperaturewere refluxed together under Dean-Stark conditions for 3 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated under reduced pressure to an oil
  4. dissolutionThis was dissolved in ethanol (30 ml)
  5. additionSolid sodium borohydride (0.040 g) was added portionwise
  6. concentrationconcentrated under reduced pressure
  7. customthe residue purified by column chromatography over silica (eluting with 9:1:0.1 dichloromethane/methanol/35% aqueous ammonia)

Quellen und Nachweise

ORD-Eintrag
ord-adc00078621443fd868cb5a37d17949c
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297818B2

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