N-Methylcyclohexylamine → N-Cyclohexyl-3, N-dimethyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate salt

HRID 2268625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268625
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[CH:17]=1)[C:12]([OH:14])=O.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:47][NH:48][CH:49]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:49]1([N:48]([CH3:47])[C:12](=[O:14])[C:11]2[CH:15]=[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[CH:17]=[C:9]([CH3:8])[CH:10]=2)[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1

Komponenten

7

Edukt 5

HCID 7514N-MethylcyclohexylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 699496943-Methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoic acid trifluoroacetate

Produkt 1

HCID 17899506N-Cyclohexyl-3, N-dimethyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzamide trifluoroacetate salt

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of 3-methyl-5-[2-(pyridin-4-ylamino)-ethoxy]-benzoic acid trifluoroacetate salt (0.031 g) in DMF (1 ml) was treated with HOBt (0.011 g), DIPEA (0.028 ml), N-methylcyclohexylamine (0.010 ml), and TBTU (0.026 g). The resulting solution was retained in a sealed flask for 64 h. The reaction mixture was concentrated under reduced pressure and the resulting gum subjected to preparative hplc. The required fraction was concentrated and then dried by addition of methanol and concentration under reduced pressure, addition of toluene and again concentration under reduced pressure giving the title compound as a colourless gum (0.034 g).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationThe required fraction was concentrated
  3. dry with materialdried by addition of methanol and concentration under reduced pressure, addition of toluene and again concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b8f9bcffdf264b1b9615023c17e7936a
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326386B1

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