Reference of 6188-43-8, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.6188-43-8, name is Imidazo[1,2-a]pyridine-3-carbaldehyde, molecular formula is C8H6N2O, molecular weight is 146.15, as common compound, the synthetic route is as follows.
b) (1S, 35)-N-(6-Fluoro-4-methylquinolin-2-yl)-N’-(imidazo [1, 2-a] pyridin-3- ylmethyl) cyclopentane-1, 3-diamine; (15, 3S)-N-(6-Fluoro-4-methylquinolin-2-yl) cyclopentane-1, 3-diamine (76 mg, 0.29 mmol) and imidazo [1, 2-a] pyridine-3-carbaldehyde (43 mg, 0.29 mmol) were dissolved in 2 mL of DCM and allowed to react for 4h. Sodium triacetoxyborohydride (112 mg, 0.53 mmol) was added and the mixture was stirred overnight. Much of the imine was left according to LC-MS. Sodium borohydride (50 mg, 1.3 mmol) was added and stirring was continued for 30 min. The mixture was acidified with 2M HCl and after 5 min the mixture was poured into water which was made alkaline with 2M NaOH. The mixture was extracted three times with EtOAc and the combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product was chromatographed on a 2 g Isolute Si column with DCM/MeOH/TEA 100/5/1. Yield: 91 mg (77%). 1H NMR (400 MHz, CDCl3) 6 8.29 (m, 1H), 7.60 (dd, 1H), 7.56 (m, 1H), 7.46 (s, 1H), 7.31 (dd, 1H), 7.23 (m, 1H), 7.13 (m, 1H), 6.77 (m, 1H), 6.46 (s, 1H), 4.85 (bd, 1H), 4.44 (m, 1H), 4.03 (s, 2H), 3.29 (m, 1H), 2.44 (bd, 3H), 2.27 (m, 1H), 2.10-1. 95 (m, 2H), 1.77 (m, 1H), 1.55-1. 35 (m, 2H). 13C NMR (100 MHz, CDC13) 6 159.9, 157.5, 156.9, 147.0, 145.7, 145.12, 145.08, 133.1, 129.2, 129.1, 125.7, 124.9, 124.8, 124.7, 123.3, 119.3, 119.1, 118.5, 113.0, 112.8, 108.6, 108.4, 58.6, 52.3, 43.0, 41.5, 33.1, 32.7, 19.7. LC-MS [M+H] + 390.2.
The chemical industry reduces the impact on the environment during synthesis 6188-43-8, I believe this compound will play a more active role in future production and life.
Reference:
Patent; ASTRAZENECA AB; WO2005/66132; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem