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Dimethylamine → N,N-dimethyl-4-[(3-nitro-4-pyridyl)oxy]cyclohexanecarboxamide

HRID 524937
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Reaktionsgleichung

Reaktionsgleichung von HRID 524937
[CH3:1][N:2](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:3].[B-](F)(F)(F)F.CNC.[N+:26]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][C:34]=1[O:35][CH:36]1[CH2:41][CH2:40][CH:39]([C:42]([OH:44])=O)[CH2:38][CH2:37]1)([O-:28])=[O:27].CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][N:2]([CH3:3])[C:42]([CH:39]1[CH2:38][CH2:37][CH:36]([O:35][C:34]2[CH:33]=[CH:32][N:31]=[CH:30][C:29]=2[N+:26]([O-:28])=[O:27])[CH2:41][CH2:40]1)=[O:44]
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Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 867209944-[(3-Nitro-4-pyridyl)oxy]cyclohexanecarboxylic acid

Produkt 1

HCID 86720996N,N-dimethyl-4-[(3-nitro-4-pyridyl)oxy]cyclohexanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

TBTU (630.0 mg, 1.962 mmol) and dimethylamine (1.784 mL of 2 M, 3.568 mmol) were added to a solution of 4-[(3-nitro-4-pyridyl)oxy]cyclohexanecarboxylic acid (475 mg, 1.784 mmol) and DIPEA (253.6 mg, 341.8 μL, 1.962 mmol) in THF (9.500 mL) and the resulting solution was stirred at RT overnight. The reaction mixture was partitioned between EtOAc and water, and the combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography on silica eluting with 0-100% EtOAc/petroleum ether using the ISCO column companion system (12 g column) Clean fractions were combined and concentrated in vacuo to yield N,N-dimethyl-4-[(3-nitro-4-pyridyl)oxy]cyclohexanecarboxamide as a pale yellow oil. (180 mg, 34%). MS (ES+) 294.3.

Aufarbeitung

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. dry with materialthe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica eluting with 0-100% EtOAc/petroleum ether using the ISCO column companion system (12 g column) Clean fractions
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a82fa909148c4e3f9c27995645e2447d
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340546B2

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