With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.220641-87-2,N-Methyltetrahydro-2H-pyran-4-amine,as a common compound, the synthetic route is as follows.
N-Methyltetrahydro-2H-pyran-4-amine (19 mg,(bromomethyl)phenyl)boronic acid (23.60 mg, 0.111 mmol) were suspended in15 acetonitrile (2 mL). K2C03 (37.9 mg, 0.275 mmol) was added, then the reaction mixture was stirred at room temperature for lOh. The reaction mixture was concentrated, dioxane (1 mL) and water (0.5 mL), phosphoric acid, potassium salt (46.6 mg, 0.22 mmol) and 7- bromo-5 -(1 -(tetrahydro-2H-pyran-4-yl)- 1 H- 1,2,3 -triazol-5 -yl)pyrrolo[2, 1 -f] [1 ,2,4]triazin- 4-amine (20 mg, 0.055 mmol) (Intermediate Ri) were added to the residue. The reaction20 vessel was evacuated, backfilled with N2 and then degassed by bubbling N2 while being sonicated. Tetrakis triphenylphosphine (7 mg, 5.49 .imol) was added and the degassing process was repeated. The reaction mixture was heated at 140 C in a microwave for 45 mm. The reaction complex was filtered, washed with water and extracted with ethyl acetate (10 mL x 3). The organic layers were combined, dried and concentrated. The25 crude mixture was purified by preparative LC method C to provide 7-(3-((methyl (tetrahydro-2H-pyran-4-yl)amino)methyl)phenyl)-5 -(1 -(tetrahydro-2H-pyran-4-yl)- 1 H- 1 ,2,3-triazol-5-yl)pyrrolo[2, 1 -f] [1 ,2,4]triazin-4-amine (8.2 mg, 41% yield). LC/MS(M+H) = 489.30. ?HNMR(500 MHz, MeOD) 5 1.72 (m, 2H), 1.85 (m, 2H), 2.01 (m,2H), 2.29 (s, 3H), 2.42 (m, 2H), 2.75 (m, 1H), 3.42 (m, 2H), 3.47 (m, 2H), 3.73 (s, 2H),4.06 (m, 4H), 4.56 (m, 1H), 6.97 (s, 1H), 7.37 (d, 2H), 7.47 (t, 1H), 7.84 (s, 1H), 7.95 (m,2H), 8.01 (s, 1H).
220641-87-2, As the paragraph descriping shows that 220641-87-2 is playing an increasingly important role.
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
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