[CH3:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]#[N:15])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H][H]>[Pd].C(O)C>[CH3:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]#[N:15])=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[N:3]=1A mixture of the product of STEP 1 (2 g), 10% Pd/C (250 mg) and ethanol (15 mL) was stirred under a balloon of hydrogen gas for 2 hr. Filtration and evaporation prodiuced the title product. 1H (CDCl3) δ 1.83 (2H, p); 2.24 (3H, s); 2.43 (2H, t); 2.62 (2H, t); 2.73 (2H, t); 3.31 (2H, m); 4.81 (1H, broad s); 6.88 (1H, s).
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