1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-nitro-5-(piperidin-1-yl)-N-(1-(3-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)benzamide

HRID 926883

Reaktionsgleichung

Reaktionsgleichung von HRID 926883
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([NH2:14])[N:11]=[CH:10]2)[CH:6]=[CH:7][CH:8]=1.[N+:17]([C:20]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:25][C:21]=1[C:22](O)=[O:23])([O-:19])=[O:18].CCN=C=NCCCN(C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[N+:17]([C:20]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:25][C:21]=1[C:22]([NH:14][C:12]1[N:11]=[CH:10][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=2)[CH:13]=1)=[O:23])([O-:19])=[O:18]

Komponenten

6

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 144593312-Nitro-5-(piperidin-1-yl)benzoic acidHCID 66520727HCID 66520727, Verbindung

Produkt 1

HCID 680697742-nitro-5-(piperidin-1-yl)-N-(1-(3-(trifluoromethyl)phenyl)-1H-imidazol-4-yl)benzamideAusbeute 29,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
28 °C

Versuchsvorschrift

Into a 250-mL round-bottom flask, was placed a solution of 1-(3-(trifluoromethyl)phenyl)-1H-imidazol-4-amine (1.2 g, 4.49 mmol, 1.00 equiv, 85%) in dichloromethane (30 mL), 2-nitro-5-(piperidin-1-yl)benzoic acid (1.32 g, 5.07 mmol, 1.00 equiv, 96%), EDC.HCl (2 g, 10.42 mmol, 2.00 equiv), and 4-dimethylaminopyridine (1.29 g, 10.57 mmol, 2.00 equiv). The resulting solution was stirred overnight at 28° C. The resulting solution was diluted with 200 mL of dichloromethane. The resulting mixture was washed with 1×30 mL of 10% sodium bicarbonate and 1×30 mL of brine, dried over sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:1) to give 600 mg (22%) of product as brown oil.

Aufarbeitung

  1. customInto a 250-mL round-bottom flask, was placed
  2. washThe resulting mixture was washed with 1×30 mL of 10% sodium bicarbonate and 1×30 mL of brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. washeluted with ethyl acetate/petroleum ether (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4dba640298734f45938cd77621e0f04c
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09289430B2

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