40117-63-3, A common heterocyclic compound, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.”40117-63-3
Step 5: (S)-4-((1-(5-(2-methoxyquinolin-1-ium-3-yl)-JH-imidazol-2-yl)- 7-(methylamino)- 7-oxoheptyl)carbamoyl)quinuclidin-1-ium mono L-tartrate salt (A5) A solution of 4-carboxyquinuclidin-1-ium chlorhydrate (1.3 eq.) in DMF (0.2 M) was treated with TBTU (1.3 eq.) and NMM (2.6 eq.). The reaction mixture was stirred at room temperature for 10 minutes and then added to a solution of A4 in DMF (0.2 M). The reaction was stirred at RT for 2 h and subsequently was purified by RP-HPLC (Acetonitrile/H20 + 0.1 % TFA). Theproduct was obtained as TFA salt which was partitioned between DCM and sat. aq. NaHCO3. The organic phase was separated, dried over Na2504 and concentrated under reduced pressure. The resulting syrup was dissolved in acetonitrile/H20 (2:3) and treated with L-tartaric acid (1 eq.). The resulting solution was lyophilized to obtain the title compound. 1H-NMR (400 MHz, 300 K, DMSO-d6) oe 8.73 (br s, 1H), 7.94 (t, 2H, J 9.6 Hz), 7.76 (d, 1H, J 8.0 Hz), 7.67 (br s,1H), 7.60 (m, 2H), 7.42 (t, 1H, J8.0 Hz), 5.02 (m, 1H), 4.13 (s, 3H), 3.93 (s, 2H), 3.18 (t, 6H, J7.2 Hz), 2.54 (d, 3H, J4.4 Hz), 2.05-1.91 (m, 8H), 1.51-1.23 (m, 8H). MS (ESj C29H38N603:519 (M+H).
The chemical industry reduces the impact on the environment during synthesis, 40117-63-3, , I believe this compound will play a more active role in future production and life.
Reference£º
Patent; IRBM SCIENCE PARK S.P.A.; C.N.C.C.S. SCARL COLLEZIONE NAZIONALE DEI COMPOSTI CHIMICI E CENTRO SCREENING; ALTAMURA, Sergio; BIANCOFIORE, Ilaria; BRESCIANI, Alberto; FERRIGNO, Federica; HARPER, Steven; LAUFER, Ralph; ONTORIA ONTORIA, Jesus Maria; MALANCONA, Savina; MONTEAGUDO, Edith; NIZI, Emanuela; ORSALE, Maria Vittoria; PONZI, Simona; PAONESSA, Giacomo; SUMMA, Vincenzo; VENEZIANO, Maria; WO2014/67985; (2014); A1;,
Quinuclidine – Wikipedia
Quinuclidine | C7H13N | ChemSpider