Acetonitrile → HCID 178457835, Verbindung

HRID 518672

Reaktionsgleichung

Reaktionsgleichung von HRID 518672
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([N+:22]([O-:24])=[O:23])=[C:7]([NH:9][C@@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:8]=1.S(Cl)(Cl)=O.C(#N)C.[NH:32]1[CH2:37][CH2:36][CH:35]([C:38]([OH:41])([CH3:40])[CH3:39])[CH2:34][CH2:33]1>C(Cl)Cl.CO>[NH4+:9].[OH-:1].[OH:41][C:38]([CH:35]1[CH2:36][CH2:37][N:32]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]([N+:22]([O-:24])=[O:23])=[C:7]([NH:9][C@@H:10]3[CH2:11][CH2:12][C@H:13]([C:16]([NH:18][CH:19]([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]3)[CH:8]=2)[CH2:33][CH2:34]1)([CH3:40])[CH3:39]

Komponenten

8

Edukt 4

HCID 6342AcetonitrileHCID 24386Thionyl ChlorideHCID 52003212-(4-Piperidyl)-2-propanolHCID 178457837HCID 178457837, Verbindung

Produkt 2

HCID 14923Ammonium HydroxideHCID 178457835HCID 178457835, VerbindungAusbeute 180,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of cis-4-(5-(hydroxymethyl)-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide (3.75 g, 11.18 mmol) in DCM (127 mL) at 0° C. was added thionyl chloride (4.08 mL, 55.9 mmol) dropwise. The reaction was stirred at 0° C. for 3 hours and then at RT for 2 hours. The reaction was concentrated in vacuo and suspended in ACN and re-concentrated to remove residual thionyl chloride. The residue was resuspended in ACN (102 mL, 11.18 mmol), cooled to 0° C., and to it was added 2-(piperidin-4-yl)propan-2-ol (5.60 g, 39.1 mmol). The reaction was stirred at RT overnight. The mixture was filtered, and the filtrate concentrated in vacuo. The residual material was purified via silica gel chromatography, eluting with 90:10:1 DCM:MeOH:NH4OH to provide cis-4-(5-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2-nitrophenylamino)-N-isopropylcyclohexanecarboxamide (4.64 g, 10.07 mmol, 90% yield) as an orange solid. MS m/z=461.4 [M+H], calc 460.61 for C25H40N4O4.

Aufarbeitung

  1. waitat RT for 2 hours
  2. concentrationThe reaction was concentrated in vacuo
  3. concentrationre-concentrated
  4. customto remove residual thionyl chloride
  5. temperaturecooled to 0° C.
  6. stirringThe reaction was stirred at RT overnight
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate concentrated in vacuo
  9. customThe residual material was purified via silica gel chromatography
  10. washeluting with 90:10:1 DCM

Quellen und Nachweise

ORD-Eintrag
ord-c3cf6107a4c94976af1aae35b8a24af8
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

Verknüpfte Notizen

Wird geladen…