6-(5-chloro-2-fluoropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine → HCID 178508356, Verbindung

HRID 1623387

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a scintillation vial containing 6-(5-chloro-2-fluoropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine (17 mg, 0.050 mmol) was added DMSO (1.3 ml) and trans-cyclohexane-1,4-diamine R2 (57.5 mg, 0.503 mmol). The homogenous reaction mixture was capped and heated to 100° C. in a oil bath for 16 hr. The reaction mixture was purified by reverse phase preparative HPLC to yield 6-(2-(trans-4-aminocyclohexylamino)-5-chloropyridin-4-yl)-N2-((tetrahydro-2H-pyran-4-yl)methyl)pyrazine-2,3-diamine (13.7 mg, 0.025 mmol, 49.9% yield), LCMS (m/z): 432.1 (MH+), retention time=0.41 min as a TFA salt after lypholyzing. 1H NMR (400 MHz, METHANOL-d4) d ppm 1.30-1.50 (m, 4H) 1.51-1.65 (m, 2H) 1.69-1.78 (m, 2H) 1.93-2.06 (m, 1H) 2.07-2.24 (m, 4H) 3.10-3.19 (m, 1H) 3.36-3.45 (m, 2H) 3.48 (d, J=6.65 Hz, 2H) 3.64-3.75 (m, 1H) 3.96 (dd, J=11.35, 3.13 Hz, 2H) 7.04-7.10 (m, 1H) 7.64 (s, 1H) 8.01 (s, 1H).

Aufarbeitung

customThe homogenous reaction mixture was capped
customThe reaction mixture was purified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-322099e20fd44e2c9e78ceee2b3b0464
Quelldatensatz: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08778951B2

Verknüpfte Notizen

Wird geladen…