反应详情

To a solution of 2-benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid (50 mg, 0.2 mmol) in DMF (2 mL), HATU (O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate) (75 mg, 0.2 mmol), 4-amino-1-(4-cyanobenzyl)piperidine dihydrochloride (47 mg, 0.2 mmol) and triethylamine (105 μL, 76 mg, 0.8 mmol) were added. The resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was poured into saturated sodium bicarbonate solution (30 mL) to give a white precipitate which was filtered and dried under vacuuo. The resulting solid was triturated with ethyl ether to yield Compound 4 as a white crystalline solid (80 mg, 97%). 1H NMR (DMSO-d6): δ 11.00 (1H, br s); 8.00 (1H, d, J=7.7 Hz); 7.82 (1H, s); 7.78 (2H, d, J=8.3 Hz); 7.53 (1H, d, J=11.8 Hz); 7.50 (2H, d, J=7.7 Hz); 7.39 (2H, d, J=6.6 Hz); 7.36 (2H, d, J=8.3 Hz); 7.32-7.23 (2H, m); 3.76 (3H, br s); 3.58 (4H, d, J=10.5 Hz); 2.89-2.73 (6H, m); 2.06 (2H, t, J=11.0 Hz); 1.76 (2H, d, J=9.9 Hz); 1.58 (2H, q, J=10.7 Hz). MS (M+H)+=504.

1. customThe resulting reaction mixture
2. customto give a white precipitate which
3. filtrationwas filtered
4. customdried under vacuuo
5. customThe resulting solid was triturated with ethyl ether