Diisopropylethylamine → HCID 178454570, Verbindung

HRID 518750

Reaktionsgleichung

Reaktionsgleichung von HRID 518750
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])[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]([NH:9][C:10](=[O:14])[CH:11]([CH3:12])[CH3:13])[CH2:7][CH2:8]2)[CH:26]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27746583-Fluoro-4-nitrobenzyl alcoholHCID 178454572HCID 178454572, Verbindung

Produkt 1

HCID 178454570HCID 178454570, VerbindungAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of N-(cis-4-aminocyclohexyl)isobutyramide hydrochloride (200 mg, 0.906 mmol) and DIPEA (0.432 mL, 2.471 mmol) in ACN (2 mL) was added (3-fluoro-4-nitrophenyl)methanol (141 mg, 0.824 mmol). The reaction was stirred overnight at 80° C. After 16 hours, the reaction mixture was concentrated and the residue purified by column chromatography, eluting with 0-100% EtOAc in DCM, to provide N-(cis-4-(5-(hydroxymethyl)-2-nitrophenylamino)cyclohexyl)isobutyramide as an orange foam (176 mg, 63.7% yield). MS, m/z (C17H25N3O4): calcd, 335.2. found, 336.0 [M+H].

Aufarbeitung

  1. waitAfter 16 hours
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue purified by column chromatography
  4. washeluting with 0-100% EtOAc in DCM

Quellen und Nachweise

ORD-Eintrag
ord-5228447a88a748f296ea13bd07153761
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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