Piperidine → cis-N-{[2-chloro-4-(1-piperidinyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide

HRID 1510957

Reaktionsgleichung

Reaktionsgleichung von HRID 1510957
C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Br[C:54]1[CH:59]=[CH:58][C:57]([CH2:60][NH:61][C:62]([CH:64]2[CH2:69][CH2:68][CH2:67][CH:66]([NH:70][C:71]3[N:76]=[C:75]([CH3:77])[N:74]=[C:73]([NH:78][CH3:79])[N:72]=3)[CH2:65]2)=[O:63])=[C:56]([Cl:80])[CH:55]=1.[NH:81]1[CH2:86][CH2:85][CH2:84][CH2:83][CH2:82]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:80][C:56]1[CH:55]=[C:54]([N:81]2[CH2:86][CH2:85][CH2:84][CH2:83][CH2:82]2)[CH:59]=[CH:58][C:57]=1[CH2:60][NH:61][C:62]([C@H:64]1[CH2:69][CH2:68][CH2:67][C@@H:66]([NH:70][C:71]2[N:76]=[C:75]([CH3:77])[N:74]=[C:73]([NH:78][CH3:79])[N:72]=2)[CH2:65]1)=[O:63]

Komponenten

7

Edukt 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67493540N-[(4-bromo-2-chlorophenyl)methyl]-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide

Produkt 1

HCID 67493595cis-N-{[2-chloro-4-(1-piperidinyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a microwave reaction vessel was added cesium carbonate (0.049 g, 0.150 mmol) under nitrogen. Next, Pd2(dba)3 (4.89 mg, 5.34 μmol), BINAP (4.99 mg, 8.02 μmol), N-[(4-bromo-2-chlorophenyl)methyl]-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide (0.050 g, 0.107 mmol) and piperidine (10.58 μl, 0.107 mmol) were then added to the reaction vial. Toluene (4.00 ml) was added and the reaction was heated to 100° C. for 16 hours. LCMS showed the formation of the desired product and the consumption of the starting materials. The reaction was cooled, the solvent was removed under vacuum, and the residue was purified by preparative HPLC to provide cis-N-{[2-chloro-4-(1-piperidinyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1,3,5-triazin-2-yl]amino}cyclohexanecarboxamide (19 mg, 0.032 mmol, 30%). MS (ES+): m/e 472, 474 [M+H]+.

Aufarbeitung

  1. customIn a microwave reaction vessel

Quellen und Nachweise

ORD-Eintrag
ord-fb0823ee512d4b278a2d7bcf3adb218c
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212032B2

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