O1CCOCC1.[Cl:7][C:8]1[N:9]=[N:10][CH:11]=[C:12](Cl)[N:13]=1.Cl.[CH3:16][CH:17]1[NH:22][CH2:21][CH2:20][N:19]2[C:23]([C:26]([F:29])([F:28])[F:27])=[N:24][CH:25]=[C:18]12.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:7][C:8]1[N:9]=[N:10][CH:11]=[C:12]([N:22]2[CH2:21][CH2:20][N:19]3[C:23]([C:26]([F:29])([F:27])[F:28])=[N:24][CH:25]=[C:18]3[CH:17]2[CH3:16])[N:13]=1To a Dioxane (12.0 ml) solution of 3,5 dichloro-1,2,4-triazine (780 mg, 5.20 mmol) was added 8-methyl-3-(trifluoromethyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine hydrochloride (CA, 1257 mg, 5.20 mmol) followed by diisopropylethylamine (2.73 ml, 15.60 mmol). Dichloromethane (2 mL) was added to solubilize the reaction. The reaction was stirred for 2 hrs at RT and then diluted with DCM. The reaction was washed with saturated sodium bicarbonate then brine, dried with sodium sulfate and concentrated to anoil. Purification of the oil on Biotage Normal Phase system (DCM:MeOH, 0-9% B) to afford the product as a solid, 1-17, (1.2 g, 71.7%). LRMS (ESI) m/z 319.1 [(M+H)+; calcd for C11H10ClF3N6: 319.1].
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