Methanol → HCID 178457841, Verbindung

HRID 518665

Reaktionsgleichung

Reaktionsgleichung von HRID 518665
Cl[C:2]1[CH:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=1.[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]([OH:33])([CH3:32])[CH3:31])[CH2:26][CH2:25]1.CO>CC(O)C>[NH4+:3].[OH-:16].[OH:33][C:30]([CH:27]1[CH2:28][CH2:29][N:24]([C:2]2[CH:7]=[C:6]([NH:8][C@@H:9]3[CH2:14][CH2:13][C@H:12]([C:15]([NH:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]3)[C:5]([N+:21]([O-:23])=[O:22])=[CH:4][N:3]=2)[CH2:25][CH2:26]1)([CH3:32])[CH3:31]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 52003212-(4-Piperidyl)-2-propanolHCID 178457831HCID 178457831, Verbindung

Produkt 2

HCID 14923Ammonium HydroxideHCID 178457841HCID 178457841, VerbindungAusbeute 200,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A suspension of cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (0.200 g, 0.587 mmol) and 2-(piperidin-4-yl)propan-2-ol (0.420 g, 2.93 mmol) in 2-propanol (2.003 mL) was microwave irradiated for 1 hour at 150° C. The reaction mixture was concentrated in vacuo, and the residual material was purified via silica gel chromatography eluting with isocratic 90:10:1 DCM:MeOH:NH4OH, to provide cis-4-(2-(4-(2-hydroxypropan-2-yl)piperidin-1-yl)-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide as a yellow solid (0.263 g, 100% yield). MS m/z=448.2 [M+H], calc 447.57 for C23H37FN5O4.

Aufarbeitung

  1. customwas microwave irradiated for 1 hour at 150° C
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residual material was purified via silica gel chromatography
  4. washeluting with isocratic 90:10:1 DCM

Quellen und Nachweise

ORD-Eintrag
ord-b165d5af108c47a4a6a00fd7e4de35a5
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115127B2

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