Acetonitrile → (2-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)benzyl)cyanamide

HRID 2075058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075058
[CH:1]1([CH:7]([O:35][CH3:36])[C:8]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:9]=2[CH2:10][NH:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:37]#[C:38]Br.C(#N)C>CO>[CH:1]1([CH:7]([O:35][CH3:36])[C:8]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][C:9]=2[CH2:10][N:11]([CH2:12][C:13]2[CH:14]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:16]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:18]=2)[C:38]#[N:37])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 10476Cyanogen BromideHCID 58968615N-(2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine

Produkt 1

HCID 86615050(2-(Cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)benzyl)cyanamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of N-(2-(cyclohexyl(methoxy)methyl)-5-(trifluoromethyl)benzyl)(3,5-bis(trifluoromethyl)phenyl)methanamine (150 mg, 0.28 mmol) and NaOAc.3H2O (77.6 mg, 0.57 mmol) in methanol was added cyanogen bromide in acetonitrile (5.0 M, 0.1 mL, 0.5 mmol). The slurry was stirred at room temperature overnight. The mixture was loaded onto a samplet and purified by chromatography over 25+S Biotage silica column (eluted with 0-30% ethyl acetate in heptane) to afford the title compound (144.1 mg, 92%). 1H NMR (400 MHz, CDCl3) δ ppm 0.91-1.19 (m, 6H) 1.41-1.53 (m, 1H) 1.62 (d, J=7.88 Hz, 2H) 1.71-1.79 (m, 1H) 1.96 (d, J=12.45 Hz, 1H) 3.16 (s, 3H) 4.00 (d, J=7.47 Hz, 1H) 4.32 (d, J=14.11 Hz, 1H) 4.32 (s, 2H) 4.40 (d, J=14.11 Hz, 1H) 7.50 (d, J=8.30 Hz, 1H) 7.54 (s, 1H) 7.63 (d, J=8.30 Hz, 1H) 7.78 (s, 2H) 7.91 (s, 1H). MS (ES−) Calc: 552.2, Found: 551.5 (M−1).

Aufarbeitung

  1. custompurified by chromatography over 25+S Biotage silica column (eluted with 0-30% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-8d6631a6587f4c099a51773374e709f4
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919506B2

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