6-(5-chloro-2-fluoropyridin-4-yl)-5-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl) pyrazin-2-amine → HCID 178432953, Verbindung

HRID 1963940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963940
[Cl:1][C:2]1[C:3]([C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:12]=[N:11][C:10]=2[CH3:23])=[CH:4][C:5](F)=[N:6][CH:7]=1.[C@H:24]1([NH2:31])[CH2:29][CH2:28][C@H:27]([NH2:30])[CH2:26][CH2:25]1>CS(C)=O>[Cl:1][C:2]1[C:3]([C:9]2[C:10]([CH3:23])=[N:11][CH:12]=[C:13]([NH:15][CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[N:14]=2)=[CH:4][C:5]([NH:30][C@H:27]2[CH2:28][CH2:29][C@H:24]([NH2:31])[CH2:25][CH2:26]2)=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 669368756-(5-chloro-2-fluoropyridin-4-yl)-5-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl) pyrazin-2-amineHCID 178511674HCID 178511674, Verbindung

Produkt 1

HCID 178432953HCID 178432953, VerbindungAusbeute 9,71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a scintillation vial containing 6-(5-chloro-2-fluoropyridin-4-yl)-5-methyl-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (7 mg, 0.021 mmol) was added DMSO and trans-cyclohexane-1,4-diamine (23.73 mg, 0.208 mmol). The homogenous reaction mixture was capped and heated to 100° C. in an oil bath for 4 hr. The crude solution was purified by reverse phase preparative HPLC to yield trans-N1-(5-chloro-4-(3-methyl-6-((tetrahydro-2H-pyran-4-yl)methyl)aminopyrazin-2-yl)pyridin-2-yl)cyclohexane-1,4-diamine (1.1 mg, 2.018 μmol, 9.71% yield), LCMS (m/z): 431.2 (MH+), retention time=0.47 min as a TFA salt after lyophilizing.

Aufarbeitung

  1. customThe homogenous reaction mixture was capped
  2. customThe crude solution was purified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-faa0822f6355421c8d053e009f52de59
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415381B2

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