Potassium Cyanide → 3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate
Reaction equation
[C:1]([O:9][CH:10]1[CH2:14][CH:13]([C:15]2[N:19]3[C:20]4[CH:26]=[CH:25][N:24](S(C5C=CC(C)=CC=5)(=O)=O)[C:21]=4[N:22]=[CH:23][C:18]3=[N:17][N:16]=2)[CH:12]([CH2:37][CH3:38])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[K+]>CO>[C:1]([O:9][CH:10]1[CH2:14][CH:13]([C:15]2[N:19]3[C:20]4[CH:26]=[CH:25][NH:24][C:21]=4[N:22]=[CH:23][C:18]3=[N:17][N:16]=2)[CH:12]([CH2:37][CH3:38])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate (5.00 g, 7.84 mmol, prepared using II from Example #4 Step J with benzoic acid and B) in MeOH (16 mL) was added a solution of potassium cyanide (0.74 mL, 17 mmol) in MeOH (16 mL). The reaction was stirred at ambient temperature for about 16 h. The reaction mixture was concd under reduced pressure to afford a residue. The residue was partitioned between water (20 mL) and DCM (20 mL). The layers were separated and the aqueous layer was extracted with DCM (3×10 mL). The extract was then washed with saturated aqueous NaHCO3, dried over anhydrous MgSO4, filtered, and concd under reduced pressure to afford a crude oil. The crude material was purified by silica gel chromatography eluting with a gradient of 0-10% MeOH in DCM to 3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl benzoate (2.30 g, 78%) as a solid. LC/MS (Table 1, Method a) Rt=2.08 min; MS m/z: 376 (M+H)+.