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1-Aminopiperidine → 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfanyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide

HRID 2215071
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2215071
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([S:13][CH3:14])=[C:11]([C:15]([OH:17])=O)[N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:46]2[CH:47]=[CH:48][CH:49]=C[C:45]=2[N:44]=[N:43]1.NN1CCCCC1>CC#N.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([S:13][CH3:14])=[C:11]([C:15]([NH:43][N:44]3[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]3)=[O:17])[N:10]=[C:9]2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 166581-AminopiperidineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 219489881-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfanyl-1H-imidazole-4-carboxylic acid

Produkt 1

HCID 21949029
1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfanyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide
Ausbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a magnetically stirred suspension of 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfanyl-1H-imidazole-4-carboxylic acid (1.72 g, 4.16 mmol) in anhydrous CH3CN (45 ml) was successively added N,N-diisopropylethylamine (Hunig's base) (1.60 ml, 9.20 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (1.89 g, 4.99 mmol) and 1-aminopiperidine (0.54 ml, 5.01 mmol). After stirring for 40 h, water was added and the resulting mixture was extracted with dichloromethane. the dichloromethane layer was successively twice washed with an 1N HCl solution and water, dried over MgSO4, filtered and concentrated to give a crude oil. This oil was further purified by flash chromatography (silicagel, EtOAc) and triturated with diethyl ether to give 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylsulfanyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide in 72% yield, mp 170° C. (dec); 1H-NMR (600 MHz, DMSO-d6) δ 1.35–1.42 (m, 2H), 1.62–1.67 (m, 4H), 2.35 (s, 3H), 2.80–2.84 (m, 4H), 7.29 (d, J=8 Hz, 2H), 7.42 (dd, J=8 and 2 Hz, 1H), 7.45 (d, J=8 Hz, 2H), 7.52 (d, J=2 Hz, 1H), 7.62 (d, J=8 Hz, 1H), 8.90 (s, 1H); 13C-NMR (150 MHz, DMSO-d6) δ 19.26, 23.32, 25.63, 55.98, 127.52, 128.61, 129.14, 129.23, 129.86, 130.12, 130.18, 133.86, 134.45, 134.66, 136.01, 137.12, 144.04, 158.98; HRMS (C22H22Cl3N4OS) [M+H]+: found m/z 495.0592, calcd 495.0580.

Aufarbeitung

  1. extractionthe resulting mixture was extracted with dichloromethane
  2. washthe dichloromethane layer was successively twice washed with an 1N HCl solution and water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude oil
  7. customThis oil was further purified by flash chromatography (silicagel, EtOAc)
  8. customtriturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-30b80428e92e4083907489f4e2d9d783
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07109216B2

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