3-Oxopropanenitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-(trifluoromethyl)piperidin-1-yl)-3-oxopropanenitrile (0.067 g, 0.18 mmol, prepared using O from 4-(trifluoromethyl)nicotinic acid, N, H with Example #5, Step C, HATU and DIEA, Q with Lawesson's reagent and mercury (II) trifluoroacetate, D with NaOH, F, H with 2-cyanoacetic acid, HATU, and DIEA) was dissolved in DMSO:MeOH (2:1, 3 mL). The mixture was separated using Varian 218 LC pumps, a Varian CVM 500 with switching valves and heaters for automatic solvent, column and temperature control and a Varian 701 Fraction collector using Method 4 (Table 2) to give 3-((3R,4R)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-(trifluoromethyl)piperidin-1-yl)-3-oxopropanenitrile (Rt=12.2 min, or =positive) (0.0284 g, 15%) [AA.1.1] and 3-((3S,4S)-3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-(trifluoromethyl)piperidin-1-yl)-3-oxopropanenitrde (Rt=5.3 min, or =negative) (0.0282 g, 15%) [AA.1.2]: LC/MS (Table 1, Method b) Rt=1.55 min; MS m/z: 377 (M+H)+. prepared The mixture was separated