StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

1-benzyl-4-methylenepiperidine → HCID 68587687, Verbindung

HRID 2070893
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2070893
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][C:10]2[N:15]3[N:16]=[C:17]([NH:19][C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)[N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:4]1)[CH3:2].C(N1CCC(=C)CC1)C1C=CC=CC=1.Br[C:45]1[N:50]2[N:51]=[C:52]([NH:54][C:55]3[CH:60]=[CH:59][C:58]([C:61]([F:64])([F:63])[F:62])=[CH:57][CH:56]=3)[N:53]=[C:49]2[CH:48]=[CH:47][CH:46]=1.C1(NC2N=C3C=CC=C(CC4CCNCC4)N3N=2)C=CC=CC=1.C(N1CCC(CC2N3N=C(NC4C=CC(C(F)(F)F)=CC=4)N=C3C=CC=2)CC1)C1C=CC=CC=1.N1CCC(CC2N3N=C(NC4C=CC(C(F)(F)F)=CC=4)N=C3C=CC=2)CC1>C(O)C.[Pd].C(O)(=O)C>[CH2:1]([N:3]1[CH2:4][CH2:5][CH:6]([CH2:9][C:10]2[N:15]3[N:16]=[C:17]([NH:19][C:20]4[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:27])[F:29])=[CH:24][CH:25]=4)[N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)[CH3:2].[F:64][C:61]([F:62])([F:63])[C:58]1[CH:59]=[CH:60][C:55]([NH:54][C:52]2[N:53]=[C:49]3[CH:48]=[CH:47][CH:46]=[CH:45][N:50]3[N:51]=2)=[CH:56][CH:57]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 6

HCID 38261121-benzyl-4-methylenepiperidineHCID 59276367HCID 59276367, VerbindungHCID 59276484HCID 59276484, VerbindungHCID 59276502HCID 59276502, VerbindungHCID 70921800HCID 70921800, VerbindungHCID 86675554HCID 86675554, Verbindung

Produkt

2
HCID 59276484HCID 59276484, VerbindungHCID 68587687HCID 68587687, VerbindungAusbeute 13,29 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

5-((1-Ethylpiperidin-4-yl)methyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. 541-Benzylpiperidin-4-yl)methyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine was synthesized from 1-benzyl-4-methylenepiperidine and 5-bromo-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine following the procedure described for N-phenyl-5-(piperidin-4-ylmethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. 5-((1-Benzylpiperidin-4-yl)methyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.165 g, 0.354 mmol) was dissolved in ethanol (30 mL) and treated with a catalytic amount of palladium on carbon (10 weight %). The reaction was stirred under an atmosphere of hydrogen gas overnight at room temperature. As only trace conversion was observed, a drop of acetic acid was added and the reaction was stirred at room temperature overnight. Most of the starting material was converted to the title compound contaminated with a minor amount of 5-(piperidin-4-ylmethyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine. The catalyst was removed by filtration washed with methanol and the filtrate was concentrated under reduced pressure. The residue was purified by semi-preparative HPLC (20-70% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, 3 injections, 30 min.). The desired fractions were combined and neutralized with a STRATA cationic resin exchange column. The eluate was concentrated under reduced pressure and dried in a vacuum oven for 5 h. 541-Ethylpiperidin-4-yl)methyl)-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine (0.019 g, 0.047 mmol, 13.29% yield) was isolated as a off-white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 10.18 (s, 1H), 7.91 (d, J=8.59 Hz, 2H), 7.64 (d, J=8.59 Hz, 2H), 7.48-7.59 (m, 2H), 6.95 (s, 1H), 3.03 (d, J=6.64 Hz, 2H), 2.82 (br s, 2H), 2.26 (s, 2H), 1.99 (br s, 1H), 1.78 (br s, 2H), 1.55 (br s, 2H), 1.33 (br s, 2H), 0.89-1.02 (m, 3H); 19F NMR (400 MHz, DMSO-d6) δ (ppm)-59.9 ppm; MS (ESI): m/z 404.2 [M+1]+.

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature overnight
  2. customThe catalyst was removed by filtration
  3. washwashed with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by semi-preparative HPLC (20-70% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, 3 injections, 30 min.)
  6. concentrationThe eluate was concentrated under reduced pressure
  7. customdried in a vacuum oven for 5 h

Quellen und Nachweise

ORD-Eintrag
ord-74cb1cd09c554421a2adbceb703f7a88
Quelldatensatz
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08299056B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion