5-chloro-6-(5-chloro-2-fluoropyridin-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine → HCID 178511609, compound

HRID 1623383Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][C:5]([NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:6][C:7]=1[C:8]1[C:13]([Cl:14])=[CH:12][N:11]=[C:10](F)[CH:9]=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:14][C:13]1[C:8]([C:7]2[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([NH:16][CH2:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[N:6]=2)=[CH:9][C:10]([NH:30][C@H:27]2[CH2:28][CH2:29][C@H:24]([NH2:31])[CH2:25][CH2:26]2)=[N:11][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a scintillation vial containing 5-chloro-6-(5-chloro-2-fluoropyridin-4-yl)-N-((tetrahydro-2H-pyran-4-yl)methyl)pyrazin-2-amine (10 mg, 0.028 mmol) and TEA (7.80 μl, 0.056 mmol) was added DMSO (1 ml) and trans-cyclohexane-1,4-diamine (32.0 mg, 0.280 mmol). The resulting homogenous reaction mixture was capped and heated to 100° C. in an oil bath for 3 hr. The reaction product was purified by reverse phase preparative HPLC to yield trans-N1-(5-chloro-4-(3-chloro-6-((tetrahydro-2H-pyran-4-yl)methyl)aminopyrazin-2-yl)pyridin-2-yl)cyclohexane-1,4-diamine (7.7 mg, 0.014 mmol, 48.6% yield), LCMS (m/z): 451.1 (MH+), retention time=0.63 min and a TFA salt after lyapholization.

Workup

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

Sources & evidence

ORD record: ord-8ebe32f4d8724d92a63d3efd4155abfb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778951B2

Reaction notes

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