2,5-Dioxopyrrolidin-1-yl 2-cyanoacetate → HCID 53358058, compound
Reaction equation
O=C1CCC(=O)N1[O:8][C:9](=O)[CH2:10][C:11]#[N:12].[NH:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([NH:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([C:27]3[CH:28]=[N:29][N:30]4[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:31]=34)[N:22]=2)[CH2:15]1>C(O)C>[C:11]([CH2:10][C:9]([N:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([NH:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([C:27]3[CH:28]=[N:29][N:30]4[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][C:31]=34)[N:22]=2)[CH2:15]1)=[O:8])#[N:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-[(2,5-Dioxopyrrolidin-1-yl)oxy]-3-oxopropanenitrile (prepared as described in BE875054(A1), 40 mg, 0.20 mmol) was added to a stirred solution of 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 7b, 60 mg, 0.16 mmol) in ethanol (1.2 mL) and the mixture was stirred at ambient temperature for 20 hours. The solvent was then removed under reduced pressure and the residue was taken-up in a mixture of dichloromethane and 4% aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried (MgSO4) and the solvent evaporated in vacuo. The crude product was purified by flash chromatography (chloroform to 40:1 chloroform/methanol) to give the title compound (20 mg, 27%) as a solid.