HCID 57504499, compound → (2S)-3-cyclobutyloxy-N-(5-methylpyrazin-2-yl)-2-[1-[3-(trifluoromethyl)pyridin-2-yl]pyrazolo[4,5-e]pyrimidin-4-yl]oxypropanamide
Reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:35]([F:38])([F:37])[F:36])[C:5]([N:8]2[C:12]3=[N:13][CH:14]=[N:15][C:16]([O:17][C@@H:18]([CH2:29][O:30][CH:31]4[CH2:34][CH2:33][CH2:32]4)[C:19]([NH:21][C:22]4[CH:27]=[N:26][C:25]([CH3:28])=[CH:24][N:23]=4)=[O:20])=[C:11]3[CH:10]=[N:9]2)=[N:6][CH:7]=1>[Pd].C(O)C>[CH:31]1([O:30][CH2:29][C@H:18]([O:17][C:16]2[C:11]3[CH:10]=[N:9][N:8]([C:5]4[C:4]([C:35]([F:37])([F:38])[F:36])=[CH:3][CH:2]=[CH:7][N:6]=4)[C:12]=3[N:13]=[CH:14][N:15]=2)[C:19]([NH:21][C:22]2[CH:27]=[N:26][C:25]([CH3:28])=[CH:24][N:23]=2)=[O:20])[CH2:32][CH2:33][CH2:34]1Participants
4
Procedure
10% Palladium on carbon (200 mg, 1.88 mmol) and (2S)-2-(1-(5-chloro-3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-cyclobutoxy-N-(5-methylpyrazin-2-yl)propanamide (Example 138) (501 mg, 0.91 mmol) in ethanol was stirred under an atmosphere of hydrogen at ambient temperature for 20 hours. The mixture was filtered and fresh catalyst (200 mg) added and the mixture stirred under hydrogen atmosphere for 8 hours. The mixture was filtered, triethylamine (1 mL) added, and the mixture evaporated. The residue was purified by flash silica chromatography eluting with ethyl acetate to give the product (150 mg, 32%). 1H NMR (400 MHz, CDCl3) δ 1.46-1.60 (1H, m), 1.64-1.71 (1H, m), 1.92-1.97 (2H, m), 2.18-2.23 (2H, m), 2.54 (3H, s), 3.98-4.07 (3H, m), 6.05 (1H, t), 7.65-7.68 (1H, m), 8.12 (1H, d), 8.29 (1H, dd), 8.44 (1H, s), 8.62-8.67 (1H, m), 8.65 (1H, s), 8.89 (1H, dd), 9.45 (1H, d); m/z (ESI+) (M+H)+=515; HPLC tR=2.25 min.