Diisopropylethylamine → HCID 178457837, Verbindung

HRID 518710

Reaktionsgleichung

Reaktionsgleichung von HRID 518710
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.F[C:25]1[CH:26]=[C:27]([CH2:34][OH:35])[CH:28]=[CH:29][C:30]=1[N+:31]([O-:33])=[O:32]>C(#N)C>[OH:35][CH2:34][C:27]1[CH:28]=[CH:29][C:30]([N+:31]([O-:33])=[O:32])=[C:25]([NH:2][C@@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]2)[CH:26]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27746583-Fluoro-4-nitrobenzyl alcoholHCID 178457872HCID 178457872, Verbindung

Produkt 1

HCID 178457837HCID 178457837, VerbindungAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of cis-4-amino-N-isopropylcyclohexanecarboxamide hydrochloride (7.09 g, 32.1 mmol) and DIPEA (15 mL, 88 mmol) in ACN (50 mL) was added (3-fluoro-4-nitrophenyl)methanol (5 g, 29.2 mmol). The reaction was stirred overnight at 80° C. The reaction mixture was concentrated, loaded onto a silica-gel pre column, and purified by column chromatography, eluting with 0-100% EtOAc in DCM, to provide cis-4-(5-(hydroxymethyl)-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide as an orange foam (7.0 g, 71.4% yield). MS, m/z (C17H25N3O4): calcd, 335.2. found, 336.0 [M+H].

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography
  3. washeluting with 0-100% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-93c854b547344db3a1358d1d90e9b33b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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