C(N(CC)CC)C.C(O[C:12](=[O:14])[CH3:13])(=O)C.[NH:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([C:28]3[CH:29]=[N:30][N:31]4[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][C:32]=34)[N:23]=2)[CH2:16]1>CN(C)C1C=CN=CC=1.ClCCl>[C:12]([N:15]1[CH2:20][CH2:19][CH2:18][C@@H:17]([NH:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]([C:28]3[CH:29]=[N:30][N:31]4[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][C:32]=34)[N:23]=2)[CH2:16]1)(=[O:14])[CH3:13]Triethylamine (44 μL, 0.32 mmol), acetic anhydride (8.2 μL, 0.09 mmol) and N,N-dimethylpyridin-4-amine (1.2 mg, 0.01 mmol) were added to a stirred solution of 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 7b, 40 mg, 0.06 mmol) in dichloromethane (1.5 mL) and the mixture was stirred at ambient temperature for 20 hours before being partitioned between dichloromethane and 4% aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with water and brine, dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (100:1 to 20:1 chloroform/methanol) to give the title compound (10 mg, 44%) as a solid.
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